Organometallic compound and organic light-emitting device including the same

ABSTRACT

An organometallic compound of Formula 1: 
     
       
         
         
             
             
         
       
     
     wherein in Formula 1, groups and variables are as described in the specification.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to Korean Patent Application No.10-2014-0086154, filed on Jul. 9, 2014, in the Korean IntellectualProperty Office, and all the benefits accruing therefrom under 35 U.S.C.§119, the content of which is incorporated herein in its entirety byreference.

BACKGROUND

1. Field

The present disclosure relates to an organometallic compound and anorganic light-emitting device including the same.

2. Description of the Related Art

Organic light emitting devices (OLEDs) are self-emission devices thathave wide viewing angles, high contrast ratios, short response times,and excellent brightness, driving voltage, and response speedcharacteristics, and produce full-color images.

A typical organic light-emitting device may include a first electrodedisposed on a substrate, and a hole transport region, an emission layer,an electron transport region, and a second electrode, which aresequentially disposed on the first electrode. Holes provided from thefirst electrode may move toward the emission layer through the holetransport region, and electrons provided from the second electrode maymove toward the emission layer through the electron transport region.Carriers, such as holes and electrons, are recombined in the emissionlayer to produce excitons. These excitons change from an excited stateto a ground state, thereby generating light.

Various types of organic light emitting devices are known. However,there still remains a need in OLEDs having low driving voltage, highefficiency, high brightness, and long lifespan.

SUMMARY

One or more embodiments relate to an organometallic compound and anorganic light-emitting device including the same.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments.

An embodiment provides an organometallic compound represented by Formula1:

wherein in Formula 1,

M is selected from a Period 1 transition metal, a Period 2 transitionmetal, and a Period 3 transition metal;

A₁ ring to A₄ ring are each independently selected from a C₆-C₂₀carbocyclic group and a C₁-C₂₀ heterocyclic group, provided that each ofthe A₃ ring and the A₄ ring is not simultaneously a benzene;

X₁ to X₄ are each independently selected from C and N;

B₁ to B₄ are each independently selected from a single bond, —O—, and—S—;

Y₁ and Y₃ are each independently selected from a single bond and adivalent linking group;

Y₂ is selected from a substituted or unsubstituted C₆-C₆₀ arylene group,a substituted or unsubstituted C₁-C₆₀ heteroarylene group, a substitutedor unsubstituted divalent non-aromatic condensed polycyclic group, and asubstituted or unsubstituted divalent non-aromatic hetero-condensedpolycyclic group;

L₁ is selected from a monodentate ligand and a bidentate ligand;

a1 is selected from 0, 1, and 2;

R₁ to R₄ are each independently selected from a hydrogen, a deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromatichetero-condensed polycyclic group, —C(═O)(Q₁), —Si(Q₁)(Q₂)(Q₃), and—N(Q₁)(Q₂); wherein R₁ and R₄ or R₂ and R₃ may be optionally linked toform a saturated or unsaturated ring;

Q₁ to Q₃ are each independently selected from a C₁-C₆₀ alkyl group and aC₆-C₆₀ aryl group;

b1 to b4 are each independently selected from 1, 2, 3, and 4;

at least one substituent of the substituted C₆-C₆₀ arylene group,substituted C₁-C₆₀ heteroarylene group, substituted divalentnon-aromatic condensed polycyclic group, the substituted divalentnon-aromatic hetero-condensed polycyclic group, substituted C₁-C₆₀ alkylgroup, substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynylgroup, substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkylgroup, substituted C₁-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₁-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₁-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group, andsubstituted monovalent non-aromatic hetero-condensed polycyclic group isselected from:

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, and a phosphoric acid group or a saltthereof; and

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic hetero-condensed polycyclic group.

In some embodiments, an organic light-emitting device includes:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the secondelectrode, wherein the organic layer includes an emission layer and ormore organometallic compounds represented by Formula 1.

The emission layer may include the organometallic compound and mayfurther include a host; and the organometallic compound may be a dopant.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readilyappreciated from the following description of the embodiments, taken inconjunction with the accompanying drawings in which:

FIG. 1 is a schematic cross-sectional view of an organic light-emittingdevice according to an embodiment.

DETAILED DESCRIPTION

Reference will now be made in detail to embodiments, examples of whichare illustrated in the accompanying drawings, wherein like referencenumerals refer to like elements throughout. In this regard, the presentembodiments may have different forms and should not be construed asbeing limited to the descriptions set forth herein. Accordingly, theembodiments are merely described below, by referring to the figures, toexplain aspects of the present description. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items. Expressions such as “at least one of” whenpreceding a list of elements, modify the entire list of elements and donot modify the individual elements of the list.

The present invention may be variously modified and have severalembodiments. Accordingly, particular embodiments will be illustrated inthe drawings and described in the detailed description in detail.Advantages, features, and how to achieve them will become apparent byreference to the embodiment that will be described later in detail,together with the accompanying drawings. This invention may, however, beembodied in many different forms and should not be limited to theexemplary embodiments.

Hereinafter, embodiments are described in detail by referring to theattached drawings, and in the drawings, like reference numerals denotelike elements, and a redundant explanation thereof will not be providedherein.

It will be understood that, although the terms first, second, third etc.may be used herein to describe various elements, components, regions,layers, and/or sections, these elements, components, regions, layers,and/or sections should not be limited by these terms. These terms areonly used to distinguish one element, component, region, layer, orsection from another element, component, region, layer, or section.Thus, a first element, component, region, layer, or section discussedbelow could be termed a second element, component, region, layer, orsection without departing from the teachings of the present embodiments.

Spatially relative terms, such as “beneath,” “below,” “lower,” “above,”“upper” and the like, may be used herein for ease of description todescribe one element or feature's relationship to another element(s) orfeature(s) as illustrated in the figures. It will be understood that thespatially relative terms are intended to encompass differentorientations of the device in use or operation in addition to theorientation depicted in the figures. For example, if the device in thefigures is turned over, elements described as “below” or “beneath” otherelements or features would then be oriented “above” the other elementsor features. Thus, the exemplary term “below” can encompass both anorientation of above and below. The device may be otherwise oriented(rotated 90 degrees or at other orientations) and the spatially relativedescriptors used herein interpreted accordingly.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting. As used herein, thesingular forms “a,” “an” and “the” are intended to include the pluralforms as well, unless the context clearly indicates otherwise.

It will be further understood that the terms “comprises” and/or“comprising,” or “includes” and/or “including” used herein specify thepresence of stated features, regions, integers, steps, operations,elements, and/or components, but do not preclude the presence oraddition of one or more other features, regions, integers, steps,operations, elements, components, and/or groups thereof.

It will be understood that when a layer, region, or component isreferred to as being “on” or “onto” another layer, region, or component,it may be directly or indirectly formed on the other layer, region, orcomponent. That is, for example, intervening layers, regions, orcomponents may be present. In contrast, when an element is referred toas being “directly on” another element, there are no interveningelements present.

Spatially relative terms, such as “beneath,” “below,” “lower,” “above,”“upper” and the like, may be used herein for ease of description todescribe one element or feature's relationship to another element(s) orfeature(s) as illustrated in the figures. It will be understood that thespatially relative terms are intended to encompass differentorientations of the device in use or operation in addition to theorientation depicted in the figures. For example, if the device in thefigures is turned over, elements described as “below” or “beneath” otherelements or features would then be oriented “above” the other elementsor features. Thus, the exemplary term “below” can encompass both anorientation of above and below. The device may be otherwise oriented(rotated 90 degrees or at other orientations) and the spatially relativedescriptors used herein interpreted accordingly.

“About” or “approximately” as used herein is inclusive of the statedvalue and means within an acceptable range of deviation for theparticular value as determined by one of ordinary skill in the art,considering the measurement in question and the error associated withmeasurement of the particular quantity (i.e., the limitations of themeasurement system). For example, “about” can mean within one or morestandard deviations, or within ±30%, 20%, 10%, 5% of the stated value.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this invention belongs. It will befurther understood that terms, such as those defined in commonly useddictionaries, should be interpreted as having a meaning that isconsistent with their meaning in the context of the relevant art and thepresent disclosure, and will not be interpreted in an idealized oroverly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to crosssection illustrations that are schematic illustrations of idealizedembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, embodiments described herein should not beconstrued as limited to the particular shapes of regions as illustratedherein but are to include deviations in shapes that result, for example,from manufacturing. For example, a region illustrated or described asflat may, typically, have rough and/or nonlinear features. Moreover,sharp angles that are illustrated may be rounded. Thus, the regionsillustrated in the figures are schematic in nature and their shapes arenot intended to illustrate the precise shape of a region and are notintended to limit the scope of the present claims.

Sizes of components in the drawings may be exaggerated for convenienceof explanation. In other words, since sizes and thicknesses ofcomponents in the drawings are arbitrarily illustrated for convenienceof explanation, the following embodiments are not limited thereto.

The term “organic layer” used herein refers to a single layer and/or aplurality of layers disposed between the first electrode and the secondelectrode of the organic light-emitting device. A material included inthe “organic layer” is not limited to an organic material.

An organometallic compound according to an embodiment is represented byFormula 1 below:

wherein in Formula 1,

M may be a transition metal.

For example, M in Formula 1 may be selected from a Period 1 transitionmetal, a Period 2 transition metal, and a Period 3 transition metal, butis not limited thereto.

In some embodiments, M in Formula 1 may be selected from a Period 3transition metal, but is not limited thereto.

In some embodiments, M in Formula 1 may be selected from a Period 3transition metal having an atomic weight of 180 or greater, but is notlimited thereto.

In some embodiments, M in Formula 1 may be selected from osmium (Os),iridium (Ir), and platinum (Pt), but is not limited thereto.

In some embodiments, M in Formula 1 may be selected from Os and Pt, butis not limited thereto.

A₁ ring to A₄ in Formula 1 ring may be each independently selected froma C₆-C₂₀ cyclic group and a C₁-C₂₀ heterocyclic group, provided thateach of the A₃ ring and the A₄ ring is not simultaneously a benzene.

For example, A₁ ring to A₄ ring in Formula 1 may be each independentlyselected from a benzene, a naphthalene, a pyrrole, an imidazole, apyrazole, a thiazole, an isothiozole, an oxazole, an isoxazole, atriazole, an indazole, a tetrahydroindazole, a pyridine, a pyrimidine, apyrazine, a pyridazine, a triazine, a quinoline, an isoquinoline, adibenzofuran, and a dibenzothiophene, but are not limited thereto. Here,each of A₃ ring and A₄ ring are not simultaneously a benzene.

In some embodiments, A₁ ring to A₄ ring in Formula 1 may be eachindependently selected from a benzene, a pyrazole, an indazole, atetrahydroindazole, a pyridine, a quinoline, an isoquinoline, and adibenzofuran, but are not limited thereto. Here, each of the A₃ ring andthe A₄ ring are not simultaneously a benzene.

In some embodiments, A₁ ring and A₂ ring in Formula 1 may be eachindependently selected from a benzene, a pyridine, a quinoline, and anisoquinoline; A₃ ring and A₄ ring may be each independently selectedfrom a benzene, a pyrazole, indazole, tetrahydroindazole, a pyridine, aquinoline, an isoquinoline, and a dibenzofuran, but are not limitedthereto. Here, each of the A₃ ring and the A₄ ring are notsimultaneously a benzene.

X₁ to X₄ in Formula 1 may be each independently selected from a carbonatom (C) and a nitrogen atom (N).

For example, in Formula 1, X₁ and X₂ may be C, and X₃ and X₄ may be N,but they are not limited thereto.

In some embodiments, in Formula 1, X₁ and X₃ may be C, and X₂ and X₄ maybe N, but they are not limited thereto.

In some embodiments, in Formula 1, X₂ and X₄ may be C, and X₁ and X₃ maybe N, but they are not limited thereto.

In some embodiments, in Formula 1, X₁ may be C, and X₂, X₃ and X₄ may beN, but they are not limited thereto.

In some embodiments, in Formula 1, X₂ may be C, and X₁, X₃ and X₄ may beN, but they are not limited thereto.

In some embodiments, in Formula 1, X₃ may be C, and X₁, X₂ and X₄ may beN, but they are not limited thereto.

In some embodiments, in Formula 1, X₄ may be C, and X₁, X₂ and X₃ may beN, but they are not limited thereto.

In some embodiments, X₁ to X₄ in Formula 1 may be N, but are not limitedthereto.

B₁ to B₄ in Formula 1 may be each independently selected from a singlebond and a divalent linking group.

For example, B₁ to B₄ in Formula 1 may be each independently selectedfrom a single bond, —O—, and —S—, but are not limited thereto.

In some embodiments, B₁ to B₄ in Formula 1 may be each independentlyselected from a single bond and —O—, but are not limited thereto.

In some embodiments, B₁ to B₄ in Formula 1 may be a single bond, but arenot limited thereto.

Y₁ and Y₃ in Formula 1 may be each independently selected from a singlebond and a divalent linking group.

For example, Y₁ and Y₃ in Formula 1 may be each independently selectedfrom a single bond, —O—, —S—, —{B(Q₁₁)}-, —{N(Q₁₂)}-,—{C(Q₁₁)(Q₁₂)}_(n1)-, —{Si(Q₁₁)(Q₁₂)}_(n1)-, a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic hetero-condensed polycyclic group;

Q₁₁ and Q₁₂ may be each independently selected from a hydrogen, adeuterium, a C₁-C₆₀ alkyl group, a C₆-C₆₀ aryl group, and a C₁-C₆₀heteroaryl group;

n1 may be selected from 1, 2, and 3;

-   -   at least one substituent of the substituted C₆-C₆₀ arylene        group, substituted C₁-C₆₀ heteroarylene group, substituted        divalent non-aromatic condensed polycyclic group, and        substituted divalent non-aromatic hetero-condensed polycyclic        group may be selected from

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, and a phosphoric acid group or a saltthereof; and

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic hetero-condensed polycyclic group, but isnot limited thereto.

In some embodiments, Y₁ and Y₃ in Formula 1 may be each independentlyselected from a single bond, —O—, —S—, —{B(Q₁₁)}-, —{N(Q₁₁)}-,—{C(Q₁₁)(Q₁₂)}_(n1)-, —{Si(Q₁₁)(Q₁₂)}_(n1)-, a phenylene group, anaphthylene group, a fluorenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a quinolinylene group, anisoquinolinylene group, a naphthyridinylene group, a quinoxalinylenegroup, a quinazolinylene group, a dibenzofuranylene group, and adibenzothiophenylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, aquinolinylene group, an isoquinolinylene group, a naphthyridinylenegroup, a quinoxalinylene group, a quinazolinylene group, adibenzofuranylene group and a dibenzothiophenylene group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a methyl group, an ethyl group, a n-propyl group, an iso-propylgroup, a n-butyl group, an iso-butyl group, a sec-butyl group, atert-butyl group, a phenyl group, and a pyridinyl group;

Q₁₁ and Q₁₂ may be each independently selected from a hydrogen, adeuterium, a methyl group, an ethyl group, a n-propyl group, aniso-propyl group, an n-butyl group, an iso-butyl group, a tert-butylgroup, and a phenyl group;

n1 may be 1, but is not limited thereto.

In some embodiments, Y₁ and Y₃ in Formula 1 may be each independentlyselected from a single bond, —O—, —S—, —N(CH₃)—, —N(Ph)-, —CH₂—,—C(CH₃)₂—, —C(CH₃)(Ph)-, —C(Ph)₂-, and Formulae 3-1 to 3-17 below, butare not limited thereto:

wherein in Formulae 3-1 to 3-17,

each of * and *′ indicates a binding site to a neighboring atom.

In some embodiments, Y₁ and Y₃ in Formula 1 may be a single bond, butare not limited thereto.

Y₂ in Formula 1 may be selected from a substituted or unsubstitutedC₆-C₆₀ arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic hetero-condensed polycyclic group;

at least one substituent of the substituted C₆-C₆₀ arylene group,substituted C₁-C₆₀ heteroarylene group, substituted divalentnon-aromatic condensed polycyclic group, and substituted divalentnon-aromatic hetero-condensed polycyclic group may be selected from

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, and a phosphoric acid group or a saltthereof; and

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic hetero-condensed polycyclic group.

For example, Y₂ in Formula 1 may be selected from a phenylene group, anaphthylene group, a fluorenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a quinolinylene group, anisoquinolinylene group, a naphthyridinylene group, a quinoxalinylenegroup, a quinazolinylene group, a dibenzofuranylene group, and adibenzothiophenylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, aquinolinylene group, an isoquinolinylene group, a naphthyridinylenegroup, a quinoxalinylene group, a quinazolinylene group, adibenzofuranylene group, and a dibenzothiophenylene group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a methyl group, an ethyl group, an n-propyl group, an iso-propylgroup, an n-butyl group, an iso-butyl group, a sec-butyl group, atert-butyl group, a phenyl group, and a pyridinyl group, but is notlimited thereto.

In some embodiments, Y₂ in Formula 1 may be selected from a phenylenegroup, a pyridinylene group, a quinolinylene group, an isoquinolinylenegroup, a dibenzofuranylene group, and a dibenzothiophenylene group; and

a phenylene group, a pyridinylene group, a quinolinylene group, anisoquinolinylene group, a dibenzofuranylene group and adibenzothiophenylene group, each substituted with at least one selectedfrom a deuterium, a methyl group, a tert-butyl group, and a phenylgroup, but is not limited thereto.

In some embodiments, Y₂ in Formula 1 may be selected from Formulae 3-1to 3-17 below, but is not limited thereto:

wherein in Formulae 3-1 to 3-17,

each of * and *′ indicates a binding site to a neighboring atom.

In some embodiments, Y₂ in Formula 1 may be selected from Formulae 3-1to 3-11 below, but is not limited thereto:

wherein in Formulae 3-1 to 3-11,

each of * and *′ indicates a binding site to a neighboring atom.

L₁ in Formula 1 may be selected from a monodentate ligand and abidentate ligand.

For example, L₁ in Formula 1 may be a monodentate ligand, but is notlimited thereto.

Examples of the monodentate ligand may include an iodide ion, a bromideion, a chloride ion, a sulfide, a thiocyanate ion, a nitrate ion, anazide ion, a hydroxyl ion, a cyanide ion, an isocyanide ion, water, anacetonitrile, a pyridine, an ammonia, a carbon monoxide, PPh₃, PPh₂CH₃,PPh(CH₃)₂, and P(CH₃)₃, but are not limited thereto.

Examples of the bidentate ligand may include a oxalate ion, anacetylacetonate, a picolinic acid, a 2-(2-hydroxyphenyl)-pyridine, a2-phenylpyridine, a 1,2-bis(diphenylphosphino)ethane (dppe), a1,1-bis(diphenylphosphino)methane (dppm), a glycinate, aethylenediamine, a 2,2′-bipyridine, and a 1,10-phenanthroline, but arenot limited thereto.

a1 in Formula 1 refers to the number of L₁ and may be selected from 0,1, and 2. When a1 is 2, two of L₁ may be identical to or different fromeach other. When a1 is 0, L₁ is absent.

For example, a1 in Formula 1 may be 0, but is not limited thereto.

In some embodiments, a1 in Formula 1 may be 2, but is not limitedthereto.

For example, in Formula 1, L₁ may be a monodentate ligand, and a1 may be2. However the present inventive concept is not limited thereto.

For example, in Formula 1, L₁ may be a bidentate ligand, and a1 maybe 1. However the present inventive concept is not limited thereto.

R₁ to R₄ In Formula 1 may be each independently selected from ahydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic hetero-condensedpolycyclic group, —C(═O)(Q₁), —Si(Q₁)(Q₂)(Q₃), and —N(Q₁)(Q₂); whereinR₁ and R₄ or R₂ and R₃ may be optionally linked to form a saturated orunsaturated ring;

Q₁ to Q₃ may be each independently selected from a C₁-C₆₀ alkyl groupand a C₆-C₆₀ aryl group;

at least one substituent of the substituted C₁-C₆₀ alkyl group,substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynyl group,substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkyl group,substituted C₁-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₁-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₁-C₆₀ heteroaryl group,substituted a monovalent non-aromatic condensed polycyclic group, andthe substituted monovalent non-aromatic hetero-condensed polycyclicgroup may be selected from

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, and a phosphoric acid group or a saltthereof; and

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic hetero-condensed polycyclic group;

For example, R₁ to R₄ in Formula 1 may be each independently selectedfrom a hydrogen, a deuterium, —F, —Cl, —Br, —I, a methyl group, an ethylgroup, an n-propyl group, an iso-propyl group, an n-butyl group, aniso-butyl group, a sec-butyl group, a tert-butyl group, —CF₃, a methoxygroup, an ethoxy group, a tert-butoxy group, a phenyl group, —C(═O)(Q₁),—Si(Q₁)(Q₂)(Q₃), and —N(Q₁)(Q₂); and

a phenyl group substituted with a methyl group; wherein R₁ and R₄ or R₂and R₃ may be optionally linked to form a saturated or unsaturated ring;

Q₁ to Q₃ may be each independently selected from a methyl group, anethyl group, an n-propyl group, an iso-propyl group, an n-butyl group,an iso-butyl group, a sec-butyl group, a tert-butyl group, and a phenylgroup, but are not limited thereto.

In some embodiments, R₁ to R₄ in Formula 1 may be each independentlyselected from a hydrogen, a deuterium, —F, a methyl group, an ethylgroup, an n-propyl group, an iso-propyl group, an iso-butyl group, asec-butyl group, a tert-butyl group, —CF₃, a methoxy group, atert-butoxy group, a phenyl group, —C(═O)(CH₃), —Si(CH₃)₃, —N(CH₃)₂,—N(Ph)₂, and a group represented by Formula 4-1 below; wherein R₁ and R₄or R₂ and R₃ may be optionally linked to form a saturated or unsaturatedring, but are not limited thereto:

wherein in Formula 4-1,

* indicates a binding site to a neighboring atom.

In some embodiments, in Formula 1, R₁ to R₄ may be each independentlyselected from a hydrogen, a methyl group, an ethyl group, an iso-propylgroup, an iso-butyl group, a sec-butyl group, a tert-butyl group, —CF₃,a phenyl group, —Si(CH₃)₃, and a group represented by Formula 4-1 below,but are not limited thereto:

wherein in Formula 4-1,

* indicates a binding site to a neighboring atom.

b1 in Formula 1 indicates the number of groups R₁ and may be selectedfrom 1, 2, 3, and 4. When b1 is 2 or greater, groups R₁ may be identicalor different.

b2 in Formula 1 indicates the number of groups R₂ and may be selectedfrom 1, 2, 3, and 4. When b2 is 2 or greater, groups R₂ may be identicalor different.

b3 in Formula 1 indicates the number of groups R₃ and may be selectedfrom 1, 2, 3, and 4. When b3 is 2 or greater, groups R₃ may be identicalor different.

b4 in Formula 1 indicates the number of groups R₄ and may be selectedfrom 1, 2, 3, and 4. When b4 is 2 or greater, groups R₄ may be identicalor different.

For example, the organometallic compound may be any one selected fromFormulae 1-1 to 1-9 below, but is not limited thereto:

wherein in Formulae 1-1 to 1-9,

M, A₁ to A₄, Y₂, L₁, a1, R₁ to R₄ and b1 to b4 in Formulae 1-1 to 1-9may be the same as in Formula 1.

In some embodiments, the organometallic compound may be one selectedfrom Formulae 1-1 to 1-9 below, but is not limited thereto:

wherein in Formulae 1-1 to 1-8,

M may be selected from osmium(Os), iridium(Ir), and platinum(Pt);

A₁ ring to A₄ ring may be each independently selected from a benzene, apyrazole, an indazole, a tetrahydroindazole, a pyridine, a quinoline, anisoquinoline, and a dibenzofuran;

Y₂ may be selected from Formulae 3-1 to 3-17 below:

wherein in Formulae 3-1 to 3-17,

each of * and *′ indicates a binding site to a neighboring atom;

R₁ to R₄ may be each independently selected from a hydrogen, a methylgroup, an ethyl group, an iso-propyl group, an iso-butyl group, asec-butyl group, a tert-butyl group, —CF₃, a phenyl group, —Si(CH₃)₃,and a group represented by Formula 4-1 below;

wherein in Formula 4-1,

* indicates a binding site to a neighboring atom.

b1 to b4 may be each independently selected from 1, 2, 3, and 4.

In some embodiments, the organometallic compound may be any one selectedfrom Formulae 1-1a to 1-6a below, but is not limited thereto:

wherein in Formulae 1-1a to 1-6a,

M, Y₂, L₁, a1, R₁ to R₄, and b1 to b4 herein may be the same as inFormula 1.

In some embodiments, the organometallic compound may be any one selectedfrom Compounds 1 to 29 below, but is not limited thereto:

The organometallic compound represented by Formula 1 has a tetradentatestructure as illustrated in Formula 1′-1 below.

The organometallic compound represented by Formula 1 has a tetradentatestructure, and thus has excellent thermal and electric stability.Accordingly, an organic light-emitting device including theorganometallic compound represented by Formula 1 has long lifespancharacteristics.

The organometallic compound represented by Formula 1, as illustrated inFormula 1′-2 below, has a divalent linking group selected from anarylene group or the like. In other words, the divalent linking group(shown inside the dotted square) in Formula 1′-2 below is not a singlebond or an alkylene group.

The organometallic compound represented by Formula 1 includes a divalentlinking group selected from an arylene group or the like, and thus has arelatively low vibrational energy. Without wishing to be bound by atheory, it is understood that nonradiative transition may relativelyrarely occur in the organometallic compound represented by Formula 1,and the organometallic compound may have a high quantum efficiency as aresult. Therefore, the organic light-emitting device including theorganometallic compound represented by Formula 1 may have highefficiency.

The organometallic compound represented by Formula 1 includes a divalentlinking group selected from an electron donating group such as anarylene group, and thus the HOMO energy level of the organometalliccompound represented by Formula 1 may be increased. In this regard, theorganic light-emitting device including the organometallic compoundrepresented by Formula 1 may have low driving voltage characteristics,and since holes are not accumulated in a transport layer, the device mayalso have high efficiency and a long lifespan.

Therefore, the organic light-emitting device including theorganometallic compound represented by Formula 1 may have a low drivingvoltage, high efficiency, and a long lifespan.

Synthesis methods to prepare the organometallic compound represented byFormula 1 are known in the art and may be apparent to one of ordinaryskill in the art by referring to Synthesis Examples provided below.

The organometallic compound represented by Formula 1 may be suitable foruse as an organic layer in an organic light-emitting device, forexample, as a dopant of an emission layer as one of the organic layers.In some embodiments, provided is an organic light-emitting deviceincluding:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the secondelectrode, wherein the organic layer includes an emission layer and atleast one selected from the organometallic compounds represented byFormula 1.

The organic light-emitting device may have, due to the inclusion of anorganic layer including the organometallic compound represented byFormula 1, low driving voltage, high efficiency, high brightness, andlong lifespan.

The organometallic compound of Formula 1 may be used between a pair ofelectrodes of an organic light-emitting device. For example, theorganometallic compound represented by Formula 1 may be included in theemission layer. In this regard, the organometallic compound may be adopant, and the emission layer may further include a host (that is, anamount of the organometallic compound represented by Formula 1 issmaller than an amount of the host).

The expression “(an organic layer) includes at least one organometalliccompound” used herein may include a case in which “(an organic layer)includes identical organometallic compounds of Formula 1 and a case inwhich (an organic layer) includes two or more different organometalliccompounds of Formula 1.

For example, the organic layer may include, as the organometalliccompound, only Compound 1. In this regard, Compound 1 may be situated inan emission layer of the organic light-emitting device. In someembodiments, the organic layer may include, as the organometalliccompound, Compound 1 and Compound 2. In this regard, Compound 1 andCompound 2 may be situated in the same layer (for example, Compound 1and Compound 2 all both be situated in an emission layer).

The first electrode may be an anode, which is a hole injectionelectrode, and the second electrode may be a cathode, which is anelectron injection electrode, or the first electrode may be a cathode,which is an electron injection electrode, or the second electrode may bean anode, which is a hole injection electrode.

For example, the first electrode is an anode, and the second electrodeis a cathode, and the organic layer includes

i) a hole transport region that is disposed between the first electrodeand the emission layer, wherein the hole transport region includes atleast one of a hole injection layer, a hole transport layer, and anelectron blocking layer, and

ii) an electron transport region that is disposed between the emissionlayer and the second electrode, wherein the electron transport regionincludes at least one selected from a hole blocking layer, an electrontransport layer, and an electron injection layer.

The term “organic layer” used herein refers to a single layer and/or aplurality of layers disposed between the first electrode and the secondelectrode of an organic light-emitting device. The “organic layer” mayinclude, in addition to an organic compound, an organometallic complexincluding a metal.

FIG. 1 is a schematic view of an organic light-emitting device 10according to an embodiment. Hereinafter, the structure of an organiclight-emitting device according to an embodiment and a method ofmanufacturing an organic light-emitting device according to anembodiment will be described in connection with FIG. 1. The organiclight-emitting device 10 includes a first electrode 11, an organic layer15, and a second electrode 19, which are sequentially stacked.

In FIG. 1, a substrate may be additionally disposed under the firstelectrode 11 or above the second electrode 19. For use as the substrate,any suitable substrate that is used in general organic light-emittingdevices may be used. The substrate may be a glass substrate ortransparent plastic substrate, each with excellent mechanical strength,thermal stability, transparency, surface smoothness, ease of handling,and water-proofness.

The first electrode 11 may be formed by depositing or sputtering amaterial for forming the first electrode on the substrate. The firstelectrode 11 may be an anode. The material for the first electrode 11may be selected from materials with a high work function to allow holesto be easily provided. The first electrode 11 may be a reflectiveelectrode or a transmissive electrode. The material for the firstelectrode 11 may be an indium tin oxide (ITO), indium zinc oxide (IZO),tin oxide (SnO₂), or zinc oxide (ZnO). In some embodiments, the materialfor the first electrode 11 may be metal, such as magnesium (Mg),aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium(Mg—In), or magnesium-silver (Mg—Ag).

The first electrode 11 may have a single-layer structure or amulti-layer structure including two or more layers. For example, thefirst electrode 11 may have a three-layered structure of ITO/Ag/ITO, butthe structure of the first electrode 110 is not limited thereto.

An organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region, an emissionlayer, and an electron transport region.

The hole transport region may be disposed between the first electrode 11and the emission layer.

The hole transport region may include at least one of a hole injectionlayer, a hole transport layer, an electron blocking layer, and a bufferlayer.

The hole transport region may include only either a hole injection layeror a hole transport layer. According to another embodiment, the holetransport region may have a structure of hole injection layer/holetransport layer or hole injection layer/hole transport layer/electronblocking layer, which are sequentially stacked in this stated order fromthe first electrode 11.

When the hole transport region includes a hole injection layer (HIL),the hole injection layer may be formed on the first electrode 11 byusing any one of various methods, for example, vacuum deposition, spincoating, casting, or Langmuir-Blodgett (LB) deposition.

When a hole injection layer is formed by vacuum deposition, thedeposition conditions may vary according to a material that is used toform the hole injection layer, and the structure and thermalcharacteristics of the hole injection layer. For example, the depositionconditions may include a deposition temperature of about 100 to about500° C., a vacuum pressure of about 10⁻⁸ to about 10⁻³ torr, and adeposition rate of about 0.01 to about 100 Angstrom per second (Å/sec).However, the deposition conditions are not limited thereto.

When the hole injection layer is formed using spin coating, coatingconditions may vary according to the material used to form the holeinjection layer, and the structure and thermal properties of the holeinjection layer. For example, a coating speed may be from about 2,000revolutions per minute (rpm) to about 5,000 rpm, and a temperature atwhich a heat treatment is performed to remove a solvent after coatingmay be from about 80° C. to about 200° C. However, the coatingconditions are not limited thereto.

Conditions for forming a hole transport layer and an electron blockinglayer may be understood by referring to conditions for forming the holeinjection layer.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, α-NPB,TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (Pani/CSA),(polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), a compoundrepresented by Formula 201 below, and a compound represented by Formula202 below:

Ar₁₀₁ and Ar₁₀₂ in Formula 201 may be each independently selected from

a phenylene, a pentalenylene, an indenylene, a naphthylene, anazulenylene, a heptalenylene, an acenaphthylene, a fluorenylene, apenalenylene, a phenanthrenylene, a anthracenylene, a fluoranthenylene,a triphenylenylene, a pyrenylene, a chrysenylenylene, a naphthacenylene,a picenylene, a perylenylene, and a pentacenylene; and

a phenylene, a pentalenylene, an indenylene, a naphthylene, anazulenylene, a heptalenylene, an acenaphthylene, a fluorenylene, apenalenylene, a phenanthrenylene, an anthracenylene, a fluoranthenylene,a triphenylenylene, a pyrenylene, a chrysenylenylene, a naphthacenylene,a picenylene, a perylenylene, and a pentacenylene, each substituted withat least one selected from a deuterium, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid and a saltthereof, a sulfonic acid and a salt thereof, a phosphoric acid and asalt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₃-C₁₀ heterocycloalkyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromatichetero-condensed polycyclic group.

xa and xb in Formula 201 may be each independently an integer of 0 to 5,or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but xa and xbare not limited thereto.

R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉, and R₁₂₁ to R₁₂₄ in Formulae 201 and 202 maybe each independently selected from

a hydrogen, a deuterium, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₁₀ alkyl (for example, methyl, ethyl, propyl, butyl, pentyl, orhexyl), and a C₁-C₁₀ alkoxy (for example, methoxy, ethoxy, propoxy,butoxy, or pentoxy);

a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted with atleast one selected from a deuterium, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid or a salt thereof, and a phosphoric acid or asalt thereof;

a phenyl, a naphthyl, an anthracenyl, a fluorenyl, and a pyrenyl; and

a phenyl, a naphthyl, an anthracenyl, a fluorenyl, and a pyrenyl, eachsubstituted with at least one selected from a deuterium, a halogen atom,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid or a salt thereof, a phosphoricacid or a salt thereof, a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxy group,but they are not limited thereto.

R₁₀₉ in Formula 201 may be one selected from a phenyl, a naphthyl, ananthracenyl, a biphenyl, and a pyridinyl; and a phenyl, a naphthyl, ananthracenyl, a biphenyl, and a pyridinyl, each substituted with at leastone selected from a deuterium, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₂₀ alkyl, and a C₁-C₂₀ alkoxy.

According to an embodiment, the compound represented by Formula 201 mayalso be represented by Formula 201A below, but is not limited thereto:

R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉ in Formula 201A may be understood byreferring to the description provided herein.

For example, the compound represented by Formula 201, and the compoundrepresented by Formula 202 may include compounds HT1 to HT20 illustratedbelow, but are not limited thereto.

A thickness of the hole transport region may be in a range of about 100Angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 1,000Å. When the hole transport region includes both a hole injection layerand a hole transport layer, a thickness of the hole injection layer maybe in a range of about 100 Å to about 10,000 Å, for example, about 100 Åto about 1,000 Å, and a thickness of the hole transport layer may be ina range of about 50 Å to about 2,000 Å, for example about 100 Å to about1,500 Å. When the thicknesses of the hole transport region, the holeinjection layer, and the hole transport layer are within these ranges,satisfactory hole transporting characteristics may be obtained without asubstantial increase in driving voltage.

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant. Thep-dopant may be one of a quinone derivative, a metal oxide, and a cyanogroup-containing compound, but is not limited thereto. Non-limitingexamples of the p-dopant include a quinone derivative, such astetracyanoquinonedimethane (TCNQ) or2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); ametal oxide, such as a tungsten oxide or a molybdenium oxide; and acyano group-containing compound, such as Compound HT-D1 below, but arenot limited thereto.

The hole transport region may include a buffer layer.

The buffer layer may compensate for an optical resonance distanceaccording to a wavelength of light emitted from the emission layer, andthus, efficiency of a formed organic light-emitting device may beimproved.

Then, an emission layer (EML) may be formed on the hole transport regionby vacuum deposition, spin coating, casting, LB deposition, or the like.When the emission layer is formed by vacuum deposition or spin coating,the deposition or coating conditions may be similar to those applied toform the hole injection layer although the deposition or coatingconditions may vary according to the material that is used to form theemission layer.

The emission layer may include a host and a dopant, and the dopant mayinclude the organometallic compound represented by Formula 1.

The host may include at least one selected from TPBi, TBADN, ADN (alsoreferred to as “DNA”), CBP, CDBP, and TCP:

According to another embodiment, the host may include a compoundrepresented by Formula 301 below.

An₁₁₁ and Ar₁₁₂ in Formula 301 may be each independently selected from aphenylene, a naphthylene, a phenanthrenylene, and a pyrenylene; and aphenylene, a naphthylene, a phenanthrenylene, a fluorenyl, and apyrenylene, each substituted with at least one selected from a phenyl, anaphthyl, and an anthracenyl.

Ar₁₁₃ to Ar₁₁₆ in Formula 301 may be each independently selected from aC₁-C₁₀ alkyl group; a phenyl, a naphthyl, a phenanthrenyl and a pyrenyl;and a phenyl, a naphthyl, a phenanthrenyl, a fluorenyl, and a pyrenyl,each substituted with at least one selected from a phenyl, a naphthyl,and an anthracenyl.

g, h, I, and j in Formula 301 may be each independently an integer of 0to 4, for example, an integer of 0, 1, or 2.

Ar₁₁₃ and Ar₁₁₆ in Formula 301 may be each independently selected from

a C₁-C₁₀ alkyl group substituted with at least one selected from aphenyl, a naphthyl, and an anthracenyl;

a phenyl, a naphthyl, an anthracenyl, a pyrenyl, a phenanthrenyl, and afluorenyl;

a phenyl, a naphthyl, an anthracenyl, a pyrenyl, a phenanthrenyl, and afluorenyl, each substituted with at least one selected from a deuterium,a halogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid and a salt thereof, a sulfonic acid and a salt thereof,a phosphoric acid and a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a phenyl,a naphthyl, an anthracenyl, a pyrenyl, a phenanthrenyl, and a fluorenyl;and

but they are not limited thereto.In some embodiments, the host may include a compound represented byFormula 302 below:

Ar₁₂₂ to Ar₁₂₅ in Formula 302 are the same as described in detail inconnection with Ar₁₁₃ in Formula 301.

Ar₁₂₆ and Ar₁₂₇ in Formula 302 may be each independently a C₁-C₁₀ alkylgroup (for example, a methyl group, an ethyl group, or a propyl group).

k and L in Formula 302 may be each independently an integer of 0 to 4.For example, k and L may be 0, 1, or 2.

The compound represented by Formula 301 and the compound represented byFormula 302 may include Compounds H1 to H42 illustrated below, but arenot limited thereto.

When the organic light-emitting device is a full color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, and a blue emission layer.According to another embodiment, due to a stack structure including ared emission layer, a green emission layer, and/or a blue emissionlayer, the emission layer may emit white light.

When the emission layer includes a host and a dopant, an amount of thedopant may be in a range of about 0.01 to about 15 parts by weight basedon 100 parts by weight of the host, but is not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within this range, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

Then, an electron transport region may be disposed on the emissionlayer.

The electron transport region may include at least one selected from ahole blocking layer, an electron transport layer, and an electroninjection layer.

For example, the electron transport region may have a structure of holeblocking layer/electron transport layer/electron injection layer or astructure of electron transport layer/electron injection layer, but thestructure of the electron transport region is not limited thereto. Theelectron transport layer may have a single-layered structure or amulti-layer structure including two or more different materials.

Conditions for forming the hole blocking layer, the electron transportlayer, and the electron injection layer which constitute the electrontransport region may be understood by referring to the conditions forforming the hole injection layer.

When the electron transport layer includes a hole blocking layer, thehole blocking layer may include, for example, at least one of BCP andBphen, but may also include other materials.

A thickness of the hole blocking layer may be in a range of about 20 Åto about 1,000 Å, for example, about 30 Å to about 300 Å. When thethickness of the hole blocking layer is within these ranges, the holeblocking layer may have excellent hole blocking characteristics withouta substantial increase in driving voltage.

The electron transport layer may further include, in addition to theorganometallic compound represented by Formula 1, at least one selectedfrom BCP, Bphen, Alq₃, Balq, TAZ, and NTAZ.

According to another embodiment, the electron transport layer mayinclude at least one of ET1 and ET2, but are not limited thereto:

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whenthe thickness of the electron transport layer is within the rangedescribed above, the electron transport layer may have satisfactoryelectron transport characteristics without a substantial increase indriving voltage.

Also, the electron transport layer may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include a Li complex. The Li complexmay include, for example, Compound ET-D1 (lithium quinolate, LiQ) orET-D2.

The electron transport region may include an electron injection layer(EIL) that allows electrons to be easily provided from a secondelectrode 19.

The electron injection layer may include at least one selected from,LiF, NaCl, CsF, Li₂O, BaO, and LiQ.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within the range describedabove, the electron injection layer may have satisfactory electroninjection characteristics without a substantial increase in drivingvoltage.

The second electrode 19 is disposed on the organic layer 15. The secondelectrode 19 may be a cathode. A material for forming the secondelectrode 19 may be metal, an alloy, an electrically conductivecompound, and a combination thereof, which have a relatively low workfunction. For example, lithium (Li), magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), ormagnesium-silver (Mg—Ag) may be formed as the material for forming thesecond electrode 19. To manufacture a top emission type light-emittingdevice, a transmissive electrode formed using ITO or IZO may be used asthe second electrode 19.

Hereinbefore, the organic light-emitting device has been described withreference to FIG. 1, but is not limited thereto.

A C₁-C₆₀ alkyl group used herein indicates a linear or branchedaliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms.Detailed examples thereof are a methyl group, an ethyl group, a propylgroup, an isobutyl group, a sec-butyl group, a tert-butyl group, apentyl group, an iso-amyl group, and a hexyl group. A C₁-C₆₀ alkylenegroup used herein indicates a divalent group having the same structureas the C₁-C₆₀ alkyl group.

A C₁-C₆₀ alkoxy group used herein indicates a monovalent grouprepresented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group). Detailedexamples thereof include a methoxy group, an ethoxy group, and anisopropyloxy group.

A C₂-C₆₀ alkenyl group used herein indicates a hydrocarbon group formedby substituting at least one carbon double bond in the middle or at theterminal of the C₂-C₆₀ alkyl group. Detailed examples thereof are anethenyl group, a propenyl group, and a butenyl group. A C₂-C₆₀alkenylene group used herein indicates a divalent group having the samestructure as the C₂-C₆₀ alkenyl group.

A C₂-C₆₀ alkynyl group used herein indicates a hydrocarbon group formedby substituting at least one carbon triple bond in the middle or at theterminal of the C₂-C₆₀ alkyl group. Detailed examples thereof are anethynyl group, and a propynyl group. A C₂-C₆₀ alkynylene group usedherein indicates a divalent group having the same structure as theC₂-C₆₀ alkynyl group.

A C₃-C₁₀ cycloalkyl group used herein indicates a monovalent hydrocarbonmonocyclic group having 3 to 10 carbon atoms. Detailed examples thereofare a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, acyclohexyl group, and a cycloheptyl group. A C₃-C₁₀ cycloalkylene groupused herein indicates a divalent group having the same structure as theC₃-C₁₀ cycloalkyl group.

A C₁-C₁₀ heterocycloalkyl group used herein indicates a monovalentmonocyclic group having at least one hetero atom selected from N, O, P,and S as a ring-forming atom and 1 to 10 carbon atoms. Detailed examplesthereof are a tetrahydrofuranyl group, and a tetrahydrothiophenyl group.A C₁-C₁₀ heterocycloalkylene group used herein indicates a divalentgroup having the same structure as the C₁-C₁₀ heterocycloalkyl group.

A C₃-C₁₀ cycloalkenyl group used herein indicates a monovalentmonocyclic group that has 3 to 10 carbon atoms and at least one doublebond in the ring thereof, which is not aromatic. Detailed examplesthereof are a cyclopentenyl group, a cyclohexenyl group, and acycloheptenyl group. A C₃-C₁₀ cycloalkenylene group used hereinindicates a divalent group having the same structure as the C₃-C₁₀cycloalkenyl group.

A C₁-C₁₀ heterocycloalkenyl group used herein indicates a monovalentmonocyclic group that has at least one hetero atom selected from N, O,P, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least onedouble bond in its ring. Detailed examples of the C₁-C₁₀heterocycloalkenyl group are a 2,3-dihydrofuranyl group and a2,3-dihydrothiophenyl group. A C₁-C₁₀ heterocycloalkenylene group usedherein indicates a divalent group having the same structure as theC₁-C₁₀ heterocycloalkenyl group.

A C₆-C₆₀ aryl group used herein indicates a monovalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms. A C₆-C₆₀arylene group used herein indicates a divalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms. Detailedexamples of the C₆-C₆₀ aryl group are a phenyl group, a naphthyl group,an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and achrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylene groupeach include two or more rings, the rings may be fused to each other.

A C₁-C₆₀ heteroaryl group used herein indicates a monovalent grouphaving a carbocyclic aromatic system that has at least one hetero atomselected from N, O, P, and S as a ring-forming atom, and 1 to 60 carbonatoms. A C₁-C₆₀ heteroarylene group used herein indicates a divalentgroup having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, P, and S as a ring-forming atom, and 1 to 60carbon atoms. Examples of the C₁-C₆₀ heteroaryl group are a pyridinylgroup, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, and an isoquinolinyl group. Whenthe C₁-C₆₀ heteroaryl group and the C₁-C₆₀ heteroarylene group eachinclude two or more rings, the rings may be fused to each other.

A C₆-C₆₀ aryloxy group used herein indicates —OA₁₀₂ (wherein A₁₀₂ is theC₆-C₆₀ aryl group), and a C₆-C₆₀ arylthio group indicates —SA₁₀₃(wherein A₁₀₃ is the C₆-C₆₀ aryl group).

A monovalent non-aromatic condensed polycyclic group used hereinindicates a monovalent group that has two or more rings condensed toeach other, only carbon atoms (for example, the number of carbon atomsmay be in a range of 8 to 60) as ring forming atoms, and which isnon-aromatic in the entire molecular structure. An example of themonovalent non-aromatic condensed polycyclic group is a fluorenyl group.A divalent non-aromatic condensed polycyclic group used herein refers toa divalent group having the same structure as the monovalentnon-aromatic condensed polycyclic group.

A monovalent non-aromatic hetero-condensed polycyclic group used hereinrefers to a monovalent group that has two or more rings condensed toeach other, has a heteroatom selected from N, O P, and S, other thancarbon atoms (for example, the number of carbon atoms may be in a rangeof 1 to 60), as ring forming atoms, and which is non-aromatic in theentire molecular structure. An example of the monovalent non-aromatichetero-condensed polycyclic group is a carbazolyl group. A divalentnon-aromatic hetero-condensed polycyclic group used herein refers to adivalent group having the same structure as the monovalent non-aromatichetero-condensed polycyclic group.

Hereinafter, a compound and an organic light-emitting device accordingto embodiments are described in detail with reference to SynthesisExamples and Examples. However, the organic light-emitting device is notlimited thereto. The wording “B was used instead of A” used indescribing Synthesis Examples means that a molar equivalent of A wasidentical to a molar equivalent of B.

SYNTHESIS EXAMPLE Synthesis Example 1 Synthesis of Compound 1

Compound 1 was synthesized according to Reaction Scheme 1 below:

1) Synthesis of Intermediate 1-4

47.0 g (150.0 mmol) of 1-bromo-3-iodobenzene was dissolved in 600 ml oftetrahydrofuran, and then, 94.0 ml (150.0 mmol) of 1.6 M n-BuLi (inhexane) was added thereto and the result was stirred at a temperature of−78° C. for about 1 hour. Next, 37 ml (180.0 mmol) of2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added thereto,and then stirred at a temperature of −78° C. for about 1 hour. Then, theresult was stirred at room temperature for about 18 hours. When thereaction is completed, 400 ml of ethyl acetate and 500 ml of brine wereadded for an extraction process, and then an organic layer was driedwith a magnesium sulfate and distilled under reduced pressure. Theresult was separation-purified by column chromatography, therebyobtaining about 38.2 g (135.0 mmol, yield of 90%) of Intermediate 1-4.The obtained compound was confirmed by LC-MS.

LC-MS m/z=284 (M+H)⁺

2) Synthesis of Intermediate 1-2

6.0 g (38.0 mmol) of 2-bromopyridine was dissolved in 300 ml oftetrahydrofuran, and then 2.2 g (1.9 mmol) of tetrakistriphenylphosphinePd(0) was added thereto at room temperature and the result was stirredfor about 5 minutes. Next, 10.8 g (38.0 mmol) of 1-bromo-3-iodobenzeneand 10.5 g (76.0 mmol) of potassium carbonate were added thereto. Then,150 ml of distilled water was added thereto and refluxed while heatingat a temperature of 70° C. for a day. When the reaction was completed,100 ml of ethyl acetate added for an extraction process, and then anorganic layer was dried with a magnesium sulfate and distilled underreduced pressure. The result was separation-purified by columnchromatography, thereby obtaining about 7.6 g (32.3 mmol, yield of 85%)of Intermediate 1-2. The obtained compound was confirmed by LC-MS.

LC-MS m/z=234 (M+H)⁺

3) Synthesis of Intermediate 1-1

6.0 g (25.6 mmol) of Intermediate 1-2 was dissolved in 200 ml of ethanoland 10 ml distilled water, and then, 0.8 g (0.6 mmol) oftetrakistriphenylphosphine Pd(0) was added thereto at room temperatureand the result was stirred for about 5 minutes. Next, 2.0 g (12.0 mmol)of Intermediate 1-3 (Reference: Organometallics 2006, 25, 349-357) and6.6 g (48.0 mmol) of potassium carbonate were added thereto, and thenthe result was refluxed while heating in a pressure flask at atemperature of 150° C. for two days. When the reaction was completed,the result was vacuum-evaporated, and 300 ml of dichloromethane and 100ml of brine were added for an extraction process. The extracted organiclayer was dried with a magnesium sulfate and distilled under reducedpressure. The result was separation-purified by column chromatography,thereby obtaining about 2.5 g (6.5 mmol, yield of 54%) of Intermediate1-1. The obtained compound was confirmed by LC-MS.

LC-MS m/z=385 (M+H)⁺

Synthesis of Compound 1

2.5 g (6.5 mmol) of Compound 1-1 was dissolved in 200 ml of acetic acid(glacial) at room temperature, and then 2.7 g (6.5 mmol) of K₂PtCl₄ andcatalytic amount of Bu₄NCl were added thereto and refluxed while heatingat 145° C. for 18 hours. After 18 hours, the result was cooled to roomtemperature, and dichloromethane and water were added for an extractionprocess. The extracted organic layer was dried with a magnesium sulfateand separation-purified by column chromatography, thereby obtainingabout 0.6 g (1.0 mmol, yield of 15%) of Compound 1.

LC-MS m/z=578 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.97-8.85 (m, 2H), 8.31-8.19 (m, 2H),7.99-7.74 (m, 6H), 7.68-7.52 (m, 4H), 7.14-7.10 (m, 2H), 6.42-6.32 (m,2H)

Synthesis Example 2 Synthesis of Compound 2

Compound 2 was synthesized according to Reaction Scheme 2 below:

1) Synthesis of Intermediate 2-2

Intermediate 2-2 (yield of 63%) was synthesized in the same manner asIntermediate 1-2 of Synthesis Example 1, except that bromoisoquinolinewas used instead of 2-bromopyridine. The obtained compound was confirmedby LC-MS.

LC-MS m/z=285 (M+H)⁺

2) Synthesis of Intermediate 2-1

Intermediate 2-1 (yield of 40%) was synthesized in the same manner asIntermediate 1-1 of Synthesis Example 1, except that Intermediate 2-2was used instead of Intermediate 1-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=485 (M+H)⁺

3) Synthesis of Compound 2

1.0 g (2.0 mmol) of Compound 2-1 was dissolved in 200 ml of acetic acid(glacial) at room temperature, and then 0.8 g (2.0 mmol) of K₂PtCl₄ andcatalytic amount of Bu₄NCl were added thereto and the result wasrefluxed while heating at a temperature of 145° C. for 18 hours. After18 hours, the result was cooled to room temperature, and dichloromethaneand water were added for an extraction process. The extracted organiclayer was dried with a magnesium sulfate and separation-purified bycolumn chromatography, thereby obtaining about 0.3 g (0.4 mmol, yield of20%) of Compound 2.

LC-MS m/z=678 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.72-8.68 (m, 2H), 8.28-8.22 (m, 2H),7.98-7.38 (m, 18H).

Synthesis Example 3 Synthesis of Compound 3

Compound 3 was synthesized according to Reaction Scheme 3 below:

1) Synthesis of Intermediate 3-2

Intermediate 3-2 (yield of 65%) was synthesized in the same manner asIntermediate 1-2 of Synthesis Example 1, except that2-bromo-5-methylpyridine was used instead of 2-bromopyridine. Theobtained compound was confirmed by LC-MS.

LC-MS m/z=248 (M+H)⁺

2) Synthesis of Intermediate 3-1

Intermediate 3-1 (yield of 50%) was synthesized in the same manner asIntermediate 1-1 of Synthesis Example 1, except that Intermediate 3-2was used instead of Intermediate 1-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=399 (M+H)⁺

3) Synthesis of Compound 3

Compound 3 (yield of 20%) was synthesized in the same manner as Compound1 of Synthesis Example 1, except that Intermediate 3-1 was used insteadof Intermediate 1-1. The obtained product was confirmed by LCMS and ¹HNMR.

LC-MS m/z=606 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.65 (s, 2H), 8.25 (d, 2H), 7.93-7.49 (m,10H), 7.12 (d, 2H), 2.32 (s, 6H).

Synthesis Example 4 Synthesis of Compound 4

Compound 4 was synthesized according to Reaction Scheme 4 below:

1) Synthesis of Intermediate 4-3

10.0 g (88.0 mmol) of 2-chloropyridine was dissolved in 200 ml oftetrahydrofuran, and then 15.6 g (96.8 mmol) of BF₃.OEt₂ was slowlyadded thereto at a temperature of 0° C. and the result was stirred at atemperature of 0° C. for about 30 minutes. Next, the result was cooledto a temperature of −78° C., and then 95.0 ml of iso-PrMgCl.LiCl (1.28 Min THF, 105.6 mmol) was slowly added thereto and the result was stirredfor 1 hour. After an hour, 43.3 g (176.0 mmol) of chloranil was addedthereto and the result was stirred at room temperature for 3 hours. Whenthe reaction was completed, aqueous ammonia and ethyl acetate were addedthereto for an extraction process, and an extracted organic layer wasdried with a magnesium sulfate and distilled under reduced pressure. Theresult was separation-purified by column chromatography, therebyobtaining about 7.5 g (48.4 mmol, yield of 55%) of Intermediate 4-3. Theobtained Compound was confirmed by LC-MS and NMR.

LC-MS m/z=156 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.27 (d, 1H), 7.17 (br s, 1H), 7.05 (d, 1H),2.99-2.80 (m, 1H), 1.26 (d, 6H)

2) Synthesis of Intermediate 4-2

Intermediate 4-4 (yield of 60%) was synthesized in the same manner asIntermediate 1-2 of Synthesis Example 1, except that Intermediate 4-3was used instead of 2-bromopyridine. The obtained compound wasidentified by LC-MS.

LC-MS m/z=277 (M+H)⁺

3) Synthesis of Intermediate 4-1

Intermediate 4-1 (yield of 60%) was synthesized in the same manner asIntermediate 1-1 of Synthesis Example 1, except that Intermediate 4-2was used instead of Intermediate 1-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=469 (M+H)⁺

4) Synthesis of Compound 4

Compound 4 (yield of 20%) was synthesized in the same manner as Compound1 of Synthesis Example 1, except that Intermediate 4-1 was used insteadof Intermediate 1-1. The obtained product was confirmed by LCMS and ¹HNMR.

LC-MS m/z=662 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.73 (d, 2H), 8.26-8.24 (m, 2H), 7.96-7.53 (m,10H), 7.09 (d, 2H), 2.84-2.82 (m, 2H), 1.23 (d, 12H).

Synthesis Example 5 Synthesis of Compound 5

Compound 5 was synthesized according to Reaction Scheme 5 below:

1) Synthesis of Intermediate 5-4

282.0 ml (141.0 mmol) of 2-methyl-1-propenylmagnesium bromide wasdissolved in 400 ml of tetrahydrofuran 400 ml, and then 154.0 ml (155.3mmol) of ZnCl₂ was slowly added thereto at a temperature of 0° C. andthe result was stirred for about 1 hour. After an hour, 20.0 g (70.6mmol) of 2-bromo-4-iodopyridine and 2.5 g (3.5 mmol) ofbis(triphenylphosphine)palladium(II) dichloride were added thereto andthe result was stirred at room temperature for 22 hours. When thereaction was completed, the result was neutralized with 4.0 N HClaqueous solution, and then dichloromethane and distilled water wereadded thereto for an extraction process. The extracted organic layer wasdried with a magnesium sulfate and distilled under reduced pressure. Theresult was separation-purified by column chromatography, therebyobtaining about 8.0 g (48.0 mmol, yield of 68%) of Intermediate 5-4. Theobtained compound was confirmed by LC-MS.

LC-MS m/z=168 (M+H)⁺

2) Synthesis of Intermediate 5-3

Intermediate 5-3 (yield of 55%) was synthesized in the same manner asIntermediate 1-2 of Synthesis Example 1, except that Intermediate 5-4was used instead of 2-bromopyridine. The obtained compound wasidentified by LC-MS.

LC-MS m/z=288 (M+H)⁺

3) Synthesis of Intermediate 5-2

Intermediate 5-2 (yield of 42%) was synthesized in the same manner asIntermediate 1-1 of Synthesis Example 1, except that Intermediate 5-3was used instead of Intermediate 1-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=493 (M+H)⁺

4) Synthesis of Intermediate 5-1

3.0 g (6.0 mmol) of Intermediate 5-2 was dissolved in 100 ml ofanhydrous methanol, and then 0.6 g (10% by weight) of Pd/C was addedthereto at room temperature; a hydrogen gas was injected thereto; andthe result was stirred at room temperature for 18 hours. When thereaction was completed, the result was filtered by celite and distilledunder reduced pressure. The result was separation-purified by columnchromatography, thereby obtaining about 2.9 g (5.90 mmol, yield of 99%)of Intermediate 5-1. The obtained compound was confirmed by LC-MS.

LC-MS m/z=497 (M+H)⁺

5) Synthesis of Compound 5

Compound 5 (yield of 15%) was synthesized in the same manner as Compound1 of Synthesis Example 1, except that Intermediate 5-1 was used insteadof Intermediate 1-1. The obtained product was confirmed by LCMS and ¹HNMR.

LC-MS m/z=690 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.56 (d, 2H), 8.25-8.22 (br s, 2H), 7.98-7.58(m, 10H), 7.06 (d, 2H), 3.26 (d, 4H), 1.85-1.83 (m, 2H), 0.92 (d, 12H).

Synthesis Example 6 Synthesis of Compound 6

Compound 6 was synthesized according to Reaction Scheme 6 below:

1) Synthesis of Intermediate 6-2

Intermediate 6-2 (yield of 65%) was synthesized in the same manner asIntermediate 1-2 of Synthesis Example 1, except that2-bromo-5-iso-propylpyridine was used instead of 2-bromopyridine. Theobtained compound was confirmed by LC-MS.

LC-MS m/z=276 (M+H)⁺

2) Synthesis of Intermediate 6-1

Intermediate 6-1 (yield of 45%) was synthesized in the same manner asIntermediate 1-1 of Synthesis Example 1, except that Intermediate 6-2was used instead of Intermediate 1-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=469 (M+H)⁺

3) Synthesis of Compound 6

Compound 6 (yield of 15%) was synthesized in the same manner as Compound1 of Synthesis Example 1, except that Intermediate 6-1 was used insteadof Intermediate 1-1. The obtained product was confirmed by LCMS and ¹HNMR.

LC-MS m/z=662 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.62 (s, 2H), 8.28 (d, 2H), 7.95-7.55 (m,10H), 7.16 (d, 2H), 2.86-2.84 (m, 2H), 1.19 (d, 12H).

Synthesis Example 7 Synthesis of Compound 7

Compound 7 was synthesized according to Reaction Scheme 7 below:

1) Synthesis of Intermediate 7-2

Intermediate 7-2 (yield of 75%) was synthesized in the same manner asIntermediate 1-2 of Synthesis Example 1, except that2-bromo-5-iso-butylpyridine (Reference for Synthesis Example: EuropeanJOC, 2011(30), 6032-6038) was used instead of 2-bromopyridine. Theobtained compound was identified by LC-MS.

LC-MS m/z=290 (M+H)⁺

2) Synthesis of Intermediate 7-1

Intermediate 7-1 (yield of 45%) was synthesized in the same manner asIntermediate 1-1 of Synthesis Example 1, except that Intermediate 7-2was used instead of Intermediate 1-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=483 (M+H)⁺

3) Synthesis of Compound 7

Compound 7 (yield of 13%) was synthesized in the same manner as Compound1 of Synthesis Example 1, except that Intermediate 7-1 was used insteadof Intermediate 1-1. The obtained product was confirmed by LCMS and ¹HNMR.

LC-MS m/z=690 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.63 (s, 2H), 8.26 (d, 2H), 7.96-7.53 (m,10H), 7.14 (d, 2H), 2.57 (s, 4H), 2.04-2.01 (m, 2H), 1.01 (d, 12H).

Synthesis Example 8 Synthesis of Compound 8

Compound 8 was synthesized according to Reaction Scheme 8 below:

1) Synthesis of Intermediate 8-2

Intermediate 8-2 (yield of 65%) was synthesized in the same manner asIntermediate 1-2 of Synthesis Example 1, except that2-chloro-4,5-dimethylpyridine a (Reference: European JOC, 2011(30),6032-6038) was used instead of 2-bromopyridine, and 98% aqueous ethanolsolution was used instead of tetrahydrofuran. The obtained compound wasidentified by LC-MS.

LC-MS m/z=262 (M+H)⁺

2) Synthesis of Intermediate 8-1

Intermediate 8-1 (yield of 42%) was synthesized in the same manner asIntermediate 1-1 of Synthesis Example 1, except that Intermediate 8-2was used instead of Intermediate 1-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=455 (M+H)⁺

3) Synthesis of Compound 8

Compound 8 (yield of 16%) was synthesized in the same manner as Compound1 of Synthesis Example 1, except that Intermediate 8-1 was used insteadof Intermediate 1-1. The obtained product was confirmed by LCMS and ¹HNMR.

LC-MS m/z=634 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.58 (s, 2H), 8.29 (d, 2H), 7.95-7.51 (m, 8H),7.21 (d, 2H), 2.36 (s, 6H), 2.34 (s, 6H).

Synthesis Example 9 Synthesis of Compound 9

Compound 9 was synthesized according to Reaction Scheme 9 below:

1) Synthesis of Intermediate 9-3

10.0 g (52.5 mmol) of 5-bromo-2-chloropyridine was dissolved in 500 mlof tetrahydrofuran, and then 3.0 g (2.6 mmol) oftetrakistriphenylphosphine Pd(0) was added thereto at room temperatureand the result was stirred for about 5 minutes. Next, 9.5 g (57.89 mmol)of 2,4,6-trimethylphenyl boronic acid and 21.8 g (157.5 mmol) ofpotassium carbonate were added thereto. Then, 250 ml of distilled waterwas added thereto and the result was refluxed while heating at atemperature of 80° C. for a day. When the reaction was completed, 200 mlof ethyl acetate was added thereto for an extraction process. Theextracted organic layer was dried with magnesium sulfate and distilledunder reduced pressure. The result was separation-purified by columnchromatography, thereby obtaining about 11.0 g (47.3 mmol, yield of 90%)of Intermediate 9-3. The obtained compound was confirmed by LC-MS.

LC-MS m/z=232 (M+H)⁺

2) Synthesis of Intermediate 9-2

Intermediate 9-2 (yield of 72%) was synthesized in the same manner asIntermediate 1-2 of Synthesis Example 1, except that Intermediate 9-3was used instead of 2-bromopyridine and 98% aqueous ethanol solution wasused instead of tetrahydrofuran. The obtained compound was identified byLC-MS.

LC-MS m/z=353 (M+H)⁺

3) Synthesis of Intermediate 9-1

Intermediate 9-1 (yield of 50%) was synthesized in the same manner asIntermediate 1-1 of Synthesis Example 1, except that Intermediate 9-2was used instead of Intermediate 1-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=621 (M+H)⁺

4) Synthesis of Compound 9

Compound 9 (yield of 15%) was synthesized in the same manner as Compound1 of Synthesis Example 1, except that Intermediate 9-1 was used insteadof Intermediate 1-1. The obtained product was confirmed by LCMS and ¹HNMR.

LC-MS m/z=814 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.87 (s, 2H), 8.26 (d, 2H), 8.03-7.70 (m,10H), 7.23 (br s, 2H), 7.03 (s, 4H), 2.87 (s, 12H), 2.52 (s, 6H).

Synthesis Example 10 Synthesis of Compound 10

Compound 10 was synthesized according to Reaction Scheme 10 below:

1) Synthesis of Intermediate 10-3

Intermediate 10-3 (yield of 81%) was synthesized in the same manner asIntermediate 9-3 of Synthesis Example 9, except that Intermediate4-bromo-2-chloropyridine was used instead of 5-bromo-2-chloropyridine.The obtained compound was confirmed by LC-MS.

LC-MS m/z=232 (M+H)⁺

2) Synthesis of Intermediate 10-2

Intermediate 10-2 (yield of 81%) was synthesized in the same manner asIntermediate 9-2 of Synthesis Example 9, except that Intermediate 10-3was used instead of 2-bromopyridine. The obtained compound was confirmedby LC-MS.

LC-MS m/z=352 (M+H)⁺

3) Synthesis of Intermediate 10-1

Intermediate 10-1 (yield of 45%) was synthesized in the same manner asIntermediate 9-1 of Synthesis Example 9, except that Intermediate 10-2was used instead of Intermediate 9-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=621 (M+H)⁺

4) Synthesis of Compound 10

Compound 10 (yield of 15%) was synthesized in the same manner asCompound 9 of Synthesis Example 9, except that Intermediate 10-1 wasused instead of Intermediate 9-1. The obtained product was confirmed byLCMS and ¹H NMR.

LC-MS m/z=814 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.72 (d, 2H), 8.51 (br s, 2H), 8.30 (br s,2H), 8.06-7.72 (m, 8H), 7.22 (br s, 2H), 7.01 (s, 4H), 2.90 (s, 12H),2.51 (s, 6H).

Synthesis Example 11 Synthesis of Compound 11

Compound 11 was synthesized according to Reaction Scheme 11 below:

1) Synthesis of Intermediate 11-3

20.0 g (84.4 mmol) of 2,5-dibromopyridine was dissolved in 300 ml ofdiethylether, and then 53 ml (84.4 mmol) of 1.6 M n-BuLi in hexane wasadded thereto at a temperature of −78° C. and the result was stirred forabout 1 hour. Next, 10.7 ml (84.4 mmol) of chlorotrimethylsilane wasslowly added thereto; the result was stirred at a temperature of −78° C.for 2 hours and then heated to room temperature; and the result wasstirred at room temperature for about 18 hours. When the reaction wascompleted, 200 ml of distilled water was added thereto, and 300 ml ofethyl acetate was added thereto for an extraction process. The extractedorganic layer was dried with magnesium sulfate and distilled underreduced pressure. The result was fractionally distilled, therebyobtaining about 16.0 g (84.0 mmol, yield of 100%) of Intermediate 11-3.The obtained compound was confirmed by LC-MS.

LC-MS m/z=186 (M+H)⁺

2) Synthesis of Intermediate 11-2

Intermediate 11-2 (yield of 65%) was synthesized in the same manner asIntermediate 1-2 of Synthesis Example 1, except that Intermediate 11-3was used instead of 2-bromopyridine, and 98% aqueous ethanol solutionwas used instead of tetrahydrofuran. The obtained compound wasidentified by LC-MS.

LC-MS m/z=306 (M+H)⁺

3) Synthesis of Intermediate 11-1

Intermediate 11-1 (yield of 53%) was synthesized in the same manner asIntermediate 1-1 of Synthesis Example 1, except that Intermediate 11-2was used instead of Intermediate 1-2. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=529 (M+H)⁺

4) Synthesis of Compound 11

Compound 11 (yield of 7%) was synthesized in the same manner as Compound1 of Synthesis Example 1, except that Intermediate 11-1 was used insteadof Intermediate 1-1. The obtained product was confirmed by LCMS and ¹HNMR.

LC-MS m/z=722 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.76 (s, 2H), 8.31 (d, 2H), 7.98-7.91 (m 2H),7.89-7.70 (m, 8H), 7.26 (br s, 2H), 0.29 (s, 18H).

Synthesis Example 12 Synthesis of Compound 12

Compound 12 was synthesized according to Reaction Scheme 12 below:

1) Synthesis of Intermediate 12-3

10.0 g (38.1 mmol) of 4-bromodibenzofuran was dissolved in 300 ml oftetrahydrofuran, and then 1.3 g (1.9 mmol) ofbis(triphenylphosphine)palladium(II) dichloride was added thereto andthe result was stirred for about 5 minutes. Next, 14.5 g (57.2 mmol) ofbis(pinacolato)diboron and 11.2 g (114.3 mmol) of potassium acetate wereadded thereto and the result was refluxed while heating at a temperatureof 80° C. for a day. When the reaction was completed, 200 ml of ethylacetate was added thereto for an extraction process, and the extractedorganic layer was dried with magnesium sulfate and distilled underreduced pressure. The result was separation-purified by columnchromatography, thereby obtaining about 10.0 g (34.3 mmol, yield of 90%)of Intermediate 12-3. The obtained compound was confirmed by LC-MS.

LC-MS m/z=295 (M+H)⁺

2) Synthesis of Intermediate 12-2

6.0 g (25.3 mmol) of 2,6-dibromipyridine was dissolved in 100 ml oftoluene, and then 1.5 g (1.3 mmol) of tetrakistriphenylphosphine Pd(0)was added thereto at room temperature and the result was stirred forabout 5 minutes. Next, 7.4 g (25.3 mmol) of Intermediate 12-3 and 8.0 g(75.9 mmol) of sodium carbonate were added thereto. Then, 30 ml ofdistilled water was added thereto and refluxed while heating for a day.When the reaction was completed, the result was filtered with diatomiteand distilled under reduced pressure. 400 ml of ethyl acetate and 100 mlof distilled water were added thereto for an extraction process. Theextracted organic layer was dried with magnesium sulfate and distilledunder reduced pressure. The result was separation-purified by columnchromatography, thereby obtaining about 4.6 g (14.2 mmol, yield of 56%)of Intermediate 12-2. The obtained compound was confirmed by LC-MS.

LC-MS m/z=325 (M+H)⁺

3) Synthesis of Intermediate 12-1

4.5 g (13.9 mmol) of Intermediate 12-2 was dissolved in 200 ml ofethanol and 10 ml of distilled water, and then 0.8 g (0.7 mmol) oftetrakistriphenylphosphine Pd(0) was added thereto at room temperatureand the result was stirred for about 5 minutes. Next, 1.1 g (6.7 mmol)of 1,3-benzenediboronic acid and 2.8 g (20.1 mmol) of potassiumcarbonate were added thereto and the result was refluxed while heatingin a pressure flask at a temperature of 150° C. for three days. When thereaction was completed, the result was vacuum-concentrated; 300 ml ofdichloromethane and 50 ml of brine was added thereto for an extractionprocess; and the extracted organic layer was dried with magnesiumsulfate and distilled under reduced pressure. The result wasseparation-purified by column chromatography, thereby obtaining about2.8 g (4.9 mmol, yield of 74%) of Intermediate 12-1. The obtainedcompound was confirmed by LC-MS.

LC-MS m/z=565 (M+H)⁺

4) Synthesis of Compound 12

Compound 12 (yield of 20%) was synthesized in the same manner asCompound 1 of Synthesis Example 1, except that Intermediate 11-1 wasused instead of Intermediate 1-1. The obtained product was confirmed byLCMS and ¹H NMR.

LC-MS m/z=758 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.92 (s, 1H), 8.67 (br s, 2H), 8.02-7.85 (m,4H), 7.81 (br s, 1H), 7.72-7.35 (m, 12H), 7.22 (br s, 2H).

Synthesis Example 13 Synthesis of Compound 13

Compound 13 was synthesized according to Reaction Scheme 13 below:

1) Synthesis of Intermediate 13-3

Intermediate 13-3 (yield of 90%) was synthesized in the same manner asIntermediate 12-3 of Synthesis Example 12, except that2-bromodibenzofuran was used instead of 4-bromodibezofuran. The obtainedcompound was confirmed by LC-MS.

LC-MS m/z=295 (M+H)⁺

2) Synthesis of Intermediate 13-2

Intermediate 13-2 (yield of 58%) was synthesized in the same manner asIntermediate 12-2 of Synthesis Example 12, except that Intermediate 13-3was used instead of Intermediate 12-3. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=323 (M+H)⁺

3) Synthesis of Intermediate 13-1

Intermediate 13-1 (yield of 65%) was synthesized in the same manner asCompound 12-1 of Synthesis Example 12, except that Intermediate 13-2 wasused instead of Intermediate 12-2. The obtained product was confirmed byLCMS and ¹H NMR.

LC-MS m/z=565 (M+H)⁺

4) Synthesis of Compound 13

Compound 13 (yield of 15%) was synthesized in the same manner asCompound 12 of Synthesis Example 12, except that Intermediate 13-1 wasused instead of Intermediate 12-1. The obtained product was confirmed byLCMS and ¹H NMR.

LC-MS m/z=758 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.95 (s, 1H), 8.46 (s, 2H), 8.42 (br s, 2H),8.01 (s, 2H), 7.99 (br s, 2H), 7.82 (br s, 1H), 7.69-7.35 (m, 10H),7.22-7.18 (m, 2H).

Synthesis Example 14 Synthesis of Compound 14

Compound 14 was synthesized according to Reaction Scheme 14 below:

1) Synthesis of Intermediate 14-4

Intermediate 14-4 (yield of 68%) was synthesized in the same manner asIntermediate 12-2 of Synthesis Example 12, except that phenylboronicacid pinacol ester was used instead of Intermediate 12-3. The obtainedcompound was confirmed by LC-MS.

LC-MS m/z=235 (M+H)⁺

2) Synthesis of Intermediate 14-3

8.5 g (36.3 mmol) of Intermediate 14-4 was dissolved in 300 ml ofethanol, and then 2.1 g (1.8 mmol) of tetrakistriphenylphosphine Pd(0)was added thereto at room temperature and the result was stirred forabout 5 minutes. Next, 6.0 g (36.3 mmol) of Intermediate 1-3 and 15.0 g(108.9 mmol) of potassium carbonate were added thereto. Then, 15 ml ofdistilled water was added thereto and the result was stirred at atemperature of 50° C. for a day. When the reaction was completed, theresult was distilled under reduced pressure, and then the obtainedcompound was extracted by adding 300 ml of dichloromethane 300 ml and 50ml of distilled water. The extracted organic layer was dried withmagnesium sulfate and distilled under reduced pressure, therebyobtaining about 10.3 g (31.2 mmol, yield of 86%) of Intermediate 14-3without a purification process. The obtained compound was confirmed byLC-MS.

LC-MS m/z=276 (M+H)⁺

3) Synthesis of Intermediate 14-2

10.0 g (30.3 mmol) of Intermediate 14-3 was dissolved in 300 ml ofethanol, and then 1.8 g (1.5 mmol) of tetrakistriphenylphosphine Pd(0)was added thereto at room temperature and the result was stirred forabout 5 minutes. Next, 10.5 g (36.3 mmol) of Intermediate 5-3 and 12.6 g(90.9 mmol) of potassium carbonate were added thereto. Then, 15 ml ofdistilled water was added thereto and the result was refluxed whileheating for a day. When the reaction was completed, the result wasdistilled under reduced pressure and the obtained compound was extractedby adding 300 ml of dichloromethane and 100 ml of brine. The extractedorganic layer was dried with magnesium sulfate and distilled underreduced pressure. The result was separation-purified by columnchromatography, thereby obtaining about 4.7 g (10.9 mmol, yield of 36%)of Intermediate. The obtained compound was confirmed by LC-MS.

LC-MS m/z=439 (M+H)⁺

4) Synthesis of Intermediate 14-1

4.5 g (10.3 mmol) of Intermediate 14-2 was dissolved in 200 ml ofanhydrous methanol; 0.5 g (10% by weight) of Pd/C was added thereto atroom temperature; a hydrogen gas was injected thereinto; and the resultwas stirred at room temperature for 24 hours. When the reaction wascompleted, the result was filtered with celite and distilled underreduced pressure. The result was separation-purified by columnchromatography, thereby obtaining about 4.5 g (10.2 mmol, yield of 99%)of Intermediate 14-1. The obtained compound was confirmed by LC-MS.

LC-MS m/z=441 (M+H)⁺

5) Synthesis of Compound 14

Compound 14 (yield of 32%) was synthesized in the same manner asCompound 1 of Synthesis Example 1, except that Intermediate 14-1 wasused instead of Intermediate 1-1. The obtained product was confirmed byLCMS and ¹H NMR.

LC-MS m/z=634 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.63 (br s, 1H), 8.35-8.22 (m, 3H), 8.07-7.85(m, 4H), 7.68-7.41 (m, 7H), 7.22 (br s, 1H), 7.06 (br s, 1H), 3.20 (d,2H), 1.84-1.82 (m, 1H), 0.90 (d, 6H).

Synthesis Example 15 Synthesis of Compound 15

Compound 15 was synthesized according to Reaction Scheme 15 below:

1) Synthesis of Intermediate 15-1

Intermediate 15-1 (yield of 35%) was synthesized in the same manner asIntermediate 14-2 of Synthesis Example 14, except that Intermediate 10-2was used instead of Intermediate 5-3. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=503 (M+H)⁺

2) Synthesis of Compound 15

Compound 15 (yield of 25%) was synthesized in the same manner asCompound 14 of Synthesis Example 14, except that Intermediate 15-1 wasused instead of Intermediate 14-1. The obtained product was confirmed byLCMS and ¹H NMR.

LC-MS m/z=696 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.70 (br s, 1H), 8.52 (br s, 1H), 8.38-8.22(m, 3H), 8.00-7.83 (m, 4H), 7.60-7.42 (m, 7H), 7.20 (br s, 1H), 7.02 (s,2H), 2.94 (s, 6H), 2.45 (s, 3H).

Synthesis Example 16 Synthesis of Compound 16

Compound 16 was synthesized according to Reaction Scheme 16 below:

1) Synthesis of Intermediate 16-5

1.05 g (26.1 mmol) of NaH was added to 150 ml of anhydroustetrahydrofuran, and then 2.1 g (21.72 mmol) of dimethyl-2-butanone wasadded thereto at a temperature of 0° C. and the result was stirred forabout 30 minutes. Next, 4.8 g (21.72 mmol) ofmethyl-6-bromopyridine-2-carboxylate dissolved in 50 ml of anhydroustetrahydrofuran was slowly added thereto at a temperature of 0° C., andthen the result was stirred for about 1 hour. After 1 hour, the resultwas stirred at a temperature of 80° C. for 18 hours. When the reactionwas completed, 50 ml of distilled water was added thereto, and anextraction process was performed three times by adding 200 ml ofmethylene chloride, thereby obtaining an organic layer. The extractedorganic layer was dried with magnesium sulfate and distilled underreduced pressure. The result was separation-purified by columnchromatography, thereby obtaining 3.3 g (11.3 mmol, yield of 52%) ofIntermediate 16-5. The obtained product was confirmed by LCMS and ¹HNMR.

LC-MS m/z=284 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.41-8.39 (m, 1H), 7.92-7.76 (m, 2H), 6.81 (s,1H), 1.15 (s, 9H)

2) Synthesis of Intermediate 16-4

3.3 g (11.3 mmol) Intermediate 16-5 was dissolved in 30 ml of ethanol,and then 57 ml (57.0 mmol) of hydrazine hydrate was added thereto, andthe result was refluxed while heating for about 24 hours. When thereaction was completed, the result was neutralized with 4 M aqueoushydrochloric acid, and concentrated in a vacuum evaporator. 100 ml ofdistilled water and 200 ml of methylene chloride were added to theconcentrated Compound for an extraction process. The extracted organiclayer was dried with magnesium sulfate and distilled under reducedpressure. The result was separation-purified by column chromatography1.8 g (6.9 mmol, yield of 60%) of Intermediate 16-4. The obtainedproduct was confirmed by LCMS and ¹H NMR.

LC-MS m/z=281 (M+H)⁺

3) Synthesis of Intermediate 16-3

1.8 g (6.9 mmol) of Intermediate 16-4 was dissolved in 80 ml of toluene,and then 0.6 g (7.2 mmol) of 3,4-dihydro-2H-pyran and 26 microliters(μl) (0.3 mmol) of trifluoroacetic acid were added thereto and theresult was refluxed while heating for about 24 hours. When the reactionwas completed, the result was distilled under reduced pressure, and theobtained Compound was extracted by adding 300 ml of dichloromethane and100 ml of brine. The extracted organic layer was dried with magnesiumsulfate and distilled under reduced pressure. The result wasseparation-purified by column chromatography, thereby obtaining about2.4 g (6.6 mmol, yield of 95%) of Intermediate 16-3. The obtainedcompound was confirmed by LC-MS.

LC-MS m/z=364 (M+H)⁺

4) Synthesis of Intermediate 16-2

Intermediate 16-2 (yield of 62%) was synthesized in the same manner asCompound 12-1 of Synthesis Example 12, except that Intermediate 16-3 wasused instead of Intermediate 12-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=645 (M+H)⁺

5) Synthesis of Intermediate 16-1

1.25 g (1.9 mmol) of Intermediate 16-2 was dissolved in 50 ml of1,4-dioxane 50 ml, and then 4.8 ml (9.5 mmol) of 2.0 N HCl in ether wasadded thereto and the result was stirred at room temperature for about18 hours. When the reaction was completed, the result was distilledunder reduced pressure, and the obtained Compound was extracted byadding 100 ml of dichloromethane and 50 ml of saturated sodium hydrogencarbonate aqueous solution. The extracted organic layer was dried withmagnesium sulfate and distilled under reduced pressure. The result wasseparation-purified by column chromatography, thereby obtaining about0.9 g (1.8 mmol, yield of 95%) of Intermediate 16-1. The obtainedcompound was confirmed by LC-MS.

LC-MS m/z=477 (M+H)⁺

6) Synthesis of Compound 16

0.09 g (3.6 mmol) of NaH was dissolved in 20 ml of anhydrousN,N-dimethylformamide (DMF), and then 0.8 g (1.8 mmol) of Intermediate16-1 was slowly added thereto at a temperature of 0° C. and the resultwas stirred at room temperature for about 1 hour. Next, 0.75 g (1.8mmol) of K₂PtCl₄ dissolved in 10 ml of distilled water was slowly addedthereto at room temperature and the result was stirred at a temperatureof 100° C. for 24 hours. After 24 hours, the result was cooled to roomtemperature, and dichloromethane and water were added for an extractionprocess. The extracted organic layer was dried with magnesium sulfateand separation-purified by column chromatography, thereby obtainingabout 0.5 g (0.8 mmol, yield of 43%) of Compound 16.

LC-MS m/z=670 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.31 (br s, 2H), 7.71 (br s, 2H), 7.45-7.38(m, 6H), 6.29 (s, 2H), 1.40 (s, 18H).

Synthesis Example 17 Synthesis of Compound 17

Compound 17 was synthesized according to Reaction Scheme 17 below:

1) Synthesis of Intermediate 17-5

Intermediate 17-5 (yield of 60%) was synthesized in the same manner asCompound 16-5 of Synthesis Example 16, except that 3-pentanone was usedinstead of dimethyl-2-butanone. The obtained compound was confirmed byLC-MS.

LC-MS m/z=270 (M+H)⁺

2) Synthesis of Intermediate 17-4

Intermediate 17-4 (yield of 60%) was synthesized in the same manner asCompound 16-4 of Synthesis Example 16, except that Intermediate 17-5 wasused instead of Intermediate 16-5. The obtained compound was confirmedby LC-MS.

LC-MS m/z=266 (M+H)⁺

3) Synthesis of Intermediate 17-3

Intermediate 17-3 (yield of ˜100%) was synthesized in the same manner asCompound 16-4 of Synthesis Example 16, except that Intermediate 17-4 wasused instead of Intermediate 16-4. The obtained compound was confirmedby LC-MS.

LC-MS m/z=350 (M+H)⁺

4) Synthesis of Intermediate 17-2

Intermediate 17-2 (yield of 55%) was synthesized in the same manner asCompound 12-1 of Synthesis Example 12, except that Intermediate 17-3 wasused instead of Intermediate 12-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=617 (M+H)⁺

5) Synthesis of Intermediate 17-1

Intermediate 17-1 (yield of −100%) was synthesized in the same manner asCompound 16-1 in Synthesis Example 16, except that Intermediate 17-2 wasused instead of Intermediate 16-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=449 (M+H)⁺

6) Synthesis of Compound 17

Compound 17 (yield of 40%) was synthesized in the same manner as used tosynthesize Compound 16 in Synthesis Example 16, except that Intermediate17-1 was used instead of Intermediate 16-1.

LC-MS m/z=642 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.33 (br s, 2H), 7.72 (br s, 2H), 7.44-7.35(m, 6H), 2.84 (q, 4H), 2.06 (s, 6H), 1.19 (t, 6H).

Synthesis Example 18 Synthesis of Compound 18

Compound 18 was synthesized according to Reaction Scheme 18 below:

1) Synthesis of Intermediate 18-5

Intermediate 18-5 (yield of 42%) was synthesized in the same manner asCompound 16-5 in Synthesis Example 16, except that cyclohexanone wasused instead of dimethyl-2-butanone.

The obtained compound was confirmed by LC-MS.

LC-MS m/z=282 (M+H)⁺

2) Synthesis of Intermediate 18-4

Intermediate 18-4 (yield of 55%) was synthesized in the same manner asCompound 16-4 in Synthesis Example 16, except that Intermediate 18-5 wasused instead of Intermediate 16-5. The obtained compound was confirmedby LC-MS.

LC-MS m/z=278 (M+H)⁺

3) Synthesis of Intermediate 18-3

Intermediate 18-3 (yield of 99%) was synthesized in the same manner asCompound 16-3 in Synthesis Example 16, except that Intermediate 18-4 wasused instead of Intermediate 16-4. The obtained compound was confirmedby LC-MS.

LC-MS m/z=362 (M+H)⁺

4) Synthesis of Intermediate 18-2

Intermediate 18-2 (yield of 55%) was synthesized in the same manner asCompound 12-1 in Synthesis Example 12, except that Intermediate 18-3 wasused instead of Intermediate 12-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=641 (M+H)⁺

5) Synthesis of Intermediate 18-1

Intermediate 18-1 (yield of −100%) was synthesized in the same manner asCompound 16-1 in Synthesis Example 16, except that Intermediate 18-2 wasused instead of Intermediate 16-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=473 (M+H)⁺

6) Synthesis of Compound 18

Intermediate 17-1 was used instead of Intermediate 16-1, and the resultwas stirred at a temperature of 100° C. for 24 hours and then cooled toroom temperature. The solid obtained from the process was filtered andwashed with methanol, thereby obtaining Compound 18 (yield of 50%). Theobtained Compound 18 was sublimation-purified.

LC-MS m/z=666 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.31 (d, 2H), 7.68 (br s, 2H), 7.51-7.44 (m,6H), 2.53-2.50 (m, 8H), 1.91-1.88 (m, 8H).

Synthesis Example 19 Synthesis of Compound 19

Compound 19 was synthesized according to Reaction Scheme 19 below:

1) Synthesis of Intermediate 19-5

Intermediate 19-5 (yield of 55%) was synthesized in the same manner asCompound 16-5 in Synthesis Example 16, except that1,1,1-trifluoroacetone was used instead of dimethyl-2-butanone. Theobtained compound was confirmed by LC-MS.

LC-MS m/z=296 (M+H)⁺

2) Synthesis of Intermediate 19-4

Intermediate 19-4 (yield of 55%) was synthesized in the same manner asCompound 16-4 in Synthesis Example 16, except that Intermediate 19-5 wasused instead of Intermediate 16-5. The obtained compound was confirmedby LC-MS.

LC-MS m/z=292 (M+H)⁺

3) Synthesis of Intermediate 19-3

Intermediate 19-3 (yield of 95%) was synthesized in the same manner asCompound 16-3 in Synthesis Example 16, except that Intermediate 19-4 wasused instead of Intermediate 16-4. The obtained compound was confirmedby LC-MS.

LC-MS m/z=376 (M+H)⁺

4) Synthesis of Intermediate 19-2

Intermediate 19-2 (yield of 46%) was synthesized in the same manner asCompound 12-1 in Synthesis Example 12, except that Intermediate 19-3 wasused instead of Intermediate 12-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=669 (M+H)⁺

5) Synthesis of Intermediate 19-1

Intermediate 19-1 (yield of ˜98%) was synthesized in the same manner asCompound 16-1 in Synthesis Example 16, except that Intermediate 19-2 wasused instead of Intermediate 16-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=501 (M+H)⁺

6) Synthesis of Compound 19

Compound 19 (yield of 35%) was synthesized in the same manner asCompound 16 in Synthesis Example 16, except that Intermediate 19-1 wasused instead of Intermediate 16-1.

LC-MS m/z=694 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.33 (br s, 2H), 7.65 (br s, 2H), 7.57-7.50(m, 6H), 6.21 (s, 2H).

Synthesis Example 20 Synthesis of Compound 20

Compound 20 was synthesized according to Reaction Scheme 20 below:

1) Synthesis of Intermediate 20-5

4.0 ml (54.5 mmol) of acetone was added to 150 ml of anhydroustetrahydrofuran, and then 55.0 ml (54.5 mmol) of 1.0 M lithiumbis(trimethylsilyl)amide solution was slowly added thereto at atemperature of −78° C. and the result was stirred for about 1 hour.After 1 hour, 9.1 g (42.0 mmol) of methyl-6-bromopyridine-2-carboxylatedissolved in 50 ml of anhydrous tetrahydrofuran was slowly added theretoat a temperature of −78° C., and the result was stirred for about 1 andthen stirred at room temperature for about 18 hours. When the reactionwas completed, 54.4 mmol of acetic acid (glacial grade) was addedthereto and the result was stirred at room temperature for 30 minutes. Asmall amount of distilled water, which is about 10 ml, and 300 ml ofdichloromethane were added for an extraction process. The extractedorganic layer was dried with magnesium sulfate and distilled underreduced pressure, thereby obtaining 6.7 g (27.7 mmol, yield of 66%) ofIntermediate 20-5 without a purification process. The obtained productwas confirmed by LCMS and ¹H NMR.

LC-MS m/z=242 (M+H)⁺

2) Synthesis of Intermediate 20-4

Intermediate 20-4 (yield of 61%) was synthesized in the same manner asCompound 16-4 in Synthesis Example 16, except that Intermediate 20-5 wasused instead of Intermediate 16-5. The obtained compound was confirmedby LC-MS.

LC-MS m/z=238 (M+H)⁺

3) Synthesis of Intermediate 20-3

Intermediate 20-3 (yield of 95%) was synthesized in the same manner asCompound 16-3 in Synthesis Example 16, except that Intermediate 20-4 wasused instead of Intermediate 16-4. The obtained compound was confirmedby LC-MS.

LC-MS m/z=322 (M+H)⁺

4) Synthesis of Intermediate 20-2

Intermediate 20-2 (yield of 42%) was synthesized in the same manner asCompound 12-1 in Synthesis Example 12, except that Intermediate 20-3 wasused instead of Intermediate 12-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=561 (M+H)⁺

5) Synthesis of Intermediate 20-1

Intermediate 20-1 (yield of −98%) was synthesized in the same manner asCompound 16-1 in Synthesis Example 16, except that Intermediate 20-2 wasused instead of Intermediate 16-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=393 (M+H)⁺

6) Synthesis of Compound 20

Compound 20 (yield of 40%) was synthesized in the same manner asCompound 16 in Synthesis Example 16, except that Intermediate 20-1 wasused instead of Intermediate 16-1.

LC-MS m/z=586 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.30 (d, 2H), 7.68 (br s, 2H), 7.45-7.40 (m,6H), 6.26 (s, 2H), 2.16 (s, 6H).

Synthesis Example 21 Synthesis of Compound 21

Compound 21 was synthesized according to Reaction Scheme 21 below:

1) Synthesis of Intermediate 21-2

Intermediate 21-2 (yield of 45%) was synthesized in the same manner asCompound 12-1 in Synthesis Example 12, except that Intermediate 17-3 wasused instead of Intermediate 12-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=617 (M+H)⁺

2) Synthesis of Intermediate 21-1

Intermediate 21-1 (yield of 98%) was synthesized in the same manner asCompound 16-1 in Synthesis Example 16, except that Intermediate 21-2 wasused instead of Intermediate 16-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=449 (M+H)⁺

3) Synthesis of Compound 21

Compound 21 (yield of 34%) was synthesized in the same manner asCompound 16 in Synthesis Example 16, except that Intermediate 21-1 wasused instead of Intermediate 16-1.

LC-MS m/z=642 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.52 (br s, 1H), 8.13 (d, 2H), 7.81 (br s,2H), 7.53-7.40 (m, 5H), 2.82 (q, 4H), 2.10 (s, 6H), 1.22 (t, 6H).

Synthesis Example 22 Synthesis of Compound 22

Compound 22 was synthesized according to Reaction Scheme 22 below:

1) Synthesis of Intermediate 22-2

Intermediate 22-2 (yield of 42%) was synthesized in the same manner asCompound 21-2 in Synthesis Example 21, except that Intermediate 18-3 wasused instead of Intermediate 17-3. The obtained compound was confirmedby LC-MS.

LC-MS m/z=669 (M+H)⁺

2) Synthesis of Intermediate 22-1

Intermediate 22-1 (yield of 98%) was synthesized in the same manner asCompound 21-1 in Synthesis Example 21, except that Intermediate 22-2 wasused instead of Intermediate 21-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=501 (M+H)⁺

3) Synthesis of Compound 22

Compound 22 (yield of 33%) was synthesized in the same manner asCompound 21 in Synthesis Example 21, except that Intermediate 22-1 wasused instead of Intermediate 21-1.

LC-MS m/z=694 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.58 (s, 1H), 8.26 (br s, 2H), 7.91 (br s,2H), 7.66-7.48 (m, 5H), 6.13 (s, 2H).

Synthesis Example 23 Synthesis of Compound 23

Compound 23 was synthesized according to Reaction Scheme 23 below:

1) Synthesis of Intermediate 23-2

Intermediate 23-2 (yield of 51%) was synthesized in the same manner asCompound 21-2 in Synthesis Example 21, except that Intermediate 18-3 wasused instead of Intermediate 17-3. The obtained compound was confirmedby LC-MS.

LC-MS m/z=641 (M+H)⁺

2) Synthesis of Intermediate 23-1

Intermediate 23-1 (yield of 98%) was synthesized in the same manner asCompound 21-1 in Synthesis Example 21, except that Intermediate 23-2 wasused instead of Intermediate 21-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=473 (M+H)⁺

3) Synthesis of Compound 23

Compound 23 (yield of 40%) was synthesized in the same manner asCompound 21 in Synthesis Example 21, except that Intermediate 23-1 wasused instead of Intermediate 21-1.

LC-MS m/z=666 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.52 (br s, 2H), 8.13 (br s, 2H), 7.98-7.95(m, 2H), 7.45-7.39 (m, 5H), 2.55-2.1 (m, 8H), 1.87-1.83 (m, 8H).

Synthesis Example 24 Synthesis of Compound 24

Compound 24 was synthesized according to Reaction Scheme 24 below:

1) Synthesis of Intermediate 24-2

Intermediate 24-2 (yield of 38%) was synthesized in the same manner asCompound 21-2 in Synthesis Example 21, except that Intermediate 20-3 wasused instead of Intermediate 17-3.

The obtained compound was confirmed by LC-MS.

LC-MS m/z=561 (M+H)⁺

2) Synthesis of Intermediate 24-1

Intermediate 24-1 (yield of 95%) was synthesized in the same manner asCompound 21-1 in Synthesis Example 21, except that Intermediate 24-2 wasused instead of Intermediate 21-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=393 (M+H)⁺

3) Synthesis of Compound 24

Compound 24 (yield of 36%) was synthesized in the same manner asCompound 21 in Synthesis Example 21, except that Intermediate 22-1 wasused instead of Intermediate 21-1.

LC-MS m/z=586 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.57 (br s, 1H), 8.30 (br s, 2H), 7.90 (br s,2H), 7.57-7.45 (m, 5H), 6.15 (s, 2H), 2.27 (s, 6H).

Synthesis Example 25 Synthesis of Compound 25

Compound 25 was synthesized according to Reaction Scheme 25 below:

1) Synthesis of Intermediate 25-2

Intermediate 25-2 (yield of 48%) was synthesized in the same manner asCompound 21-2 in Synthesis Example 21, except that p-tolylboronic acidwas used instead of 1,3-benzenediboronic acid. The obtained compound wasconfirmed by LC-MS.

LC-MS m/z=631 (M+H)⁺

2) Synthesis of Intermediate 25-1

Intermediate 25-1 (yield of 97%) was synthesized in the same manner asCompound 21-1 in Synthesis Example 21, except that Intermediate 25-2 wasused instead of Intermediate 21-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=463 (M+H)⁺

3) Synthesis of Compound 25

Compound 25 (yield of 33%) was synthesized in the same manner asCompound 21 in Synthesis Example 21, except that Intermediate 25-1 wasused instead of Intermediate 21-1.

LC-MS m/z=656 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.50 (s, 1H), 8.18 (s, 2H), 7.73-7.70 (m, 2H),7.55-7.44 (m, 4H), 2.83 (q, 4H), 2.33 (s, 3H), 2.09 (s, 6H), 1.20 (t,6H).

Synthesis Example 26 Synthesis of Compound 26

Compound 26 was synthesized according to Reaction Scheme 26 below:

1) Synthesis of Intermediate 26-2

Intermediate 26-2 (yield of 45%) was synthesized in the same manner asCompound 21-2 in Synthesis Example 21, except that3,5-dimethylphenylboronic acid was used instead of 1,3-benzenediboronicacid. The obtained compound was confirmed by LC-MS.

LC-MS m/z=645 (M+H)⁺

2) Synthesis of Intermediate 26-1

Intermediate 26-1 (yield of 97%) was synthesized in the same manner asCompound 21-1 in Synthesis Example 21, except that Intermediate 25-2 wasused instead of Intermediate 21-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=477 (M+H)⁺

3) Synthesis of Compound 26

Compound 26 (yield of 35%) was synthesized in the same manner asCompound 21 in Synthesis Example 21, except that Intermediate 26-1 wasused instead of Intermediate 21-1.

LC-MS m/z=670 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.55 (br s, 1H), 7.76-7.72 (m, 2H), 7.52-7.31(m, 6H), 2.85 (q, 4H), 2.38 (s, 6H), 2.12 (s, 6H), 1.22 (t, 6H).

Synthesis Example 27 Synthesis of Compound 27

Compound 27 was synthesized according to Reaction Scheme 27 below:

1) Synthesis of Intermediate 27-5

3.0 g (34.8 mmol) of 3-pentanone was added to 150 ml of anhydroustetrahydrofuran, and then 35 ml (35.0 mmol) of 1.0 M LiHMDS in THF wasslowly added thereto at a temperature of −78° C. and the result wasstirred for about 1 hour. Next, 6.2 g (26.8 mmol) of ethyl4-bromopyrimidine-2-carboxylate dissolved in anhydrous tetrahydrofuranwas slowly added thereto at a temperature of −78° C., and the result wasstirred for about 1 hour. After 1 hour, the result was stirred at roomtemperature for 24 hours. When the reaction was completed, 2 ml ofacetic acid (glacial grade) 2 ml was added thereto and the result wasstirred for about 30 minutes. After 30 minutes, 10 ml of distilled waterand 200 ml of methylene chloride were added thereto for an extractionprocess. Then, the extracted organic layer was dried with magnesiumsulfate and distilled under reduced pressure. The result wasseparation-purified by column chromatography, thereby obtaining 3.5 g(12.9 mmol, yield of 48%) of Intermediate 27-5. The obtained compoundwas confirmed by LC-MS.

LC-MS m/z=271 (M+H)⁺

2) Synthesis of Intermediate 27-4

Intermediate 27-4 (yield of 55%) was synthesized in the same manner asCompound 16-4 in Synthesis Example 16, except that Intermediate 27-5 wasused instead of Intermediate 16-5.

The obtained compound was confirmed by LC-MS.

LC-MS m/z=267 (M+H)⁺

3) Synthesis of Intermediate 27-3

Intermediate 27-3 (yield of 98%) was synthesized in the same manner asCompound 16-3 in Synthesis Example 16, except that Intermediate 27-4 wasused instead of Intermediate 16-4.

The obtained compound was confirmed by LC-MS.

LC-MS m/z=351 (M+H)⁺

4) Synthesis of Intermediate 27-2

Intermediate 27-2 (yield of 40%) was synthesized in the same manner asCompound 21-2 in Synthesis Example 21, except that Intermediate 27-3 wasused instead of Intermediate 21-3. The obtained compound was confirmedby LC-MS.

LC-MS m/z=619 (M+H)⁺

5) Synthesis of Intermediate 27-1

Intermediate 27-1 (yield of 98%) was synthesized in the same manner asCompound 21-1 in Synthesis Example 21, except that Intermediate 27-2 wasused instead of Intermediate 21-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=451 (M+H)⁺

6) Synthesis of Compound 27

Compound 27 (yield of 30%) was synthesized in the same manner asCompound 21 in Synthesis Example 21, except that Intermediate 27-1 wasused instead of Intermediate 21-1. LC-MS m/z=644 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=8.66 (d, 1H), 8.10 (d, 2H), 8.02-7.99 (m, 3H),7.41 (br s, 1H), 2.81 (q, 4H), 2.12 (s, 6H), 1.26 (t, 6H).

Synthesis Example 28 Synthesis of Compound 28

Compound 28 was synthesized according to Reaction Scheme 28 below:

1) Synthesis of Intermediate 28-3

5.0 g (21.4 mmol) of Intermediate 1-2 was dissolved in 200 ml ofethanol, and then 1.2 g (1.1 mmol) tetrakistriphenylphosphine Pd(0) wasadded thereto at room temperature and the result was stirred for about 5minutes. Next, 3.6 g (21.4 mmol) of 1,3-benzenediboronic acid and 8.9 g(64.2 mmol) of potassium carbonate were added thereto. Then, 10 ml ofdistilled water was added thereto and the result was stirred at atemperature of 50° C. for two days. When the reaction was completed, theresult was distilled under reduced pressure and the obtained Compoundwas extracted by adding 300 ml of dichloromethane 300 ml and 50 ml ofdistilled water. The extracted organic layer was dried with magnesiumsulfate and distilled under reduced pressure, thereby obtaining about3.8 g (13.9 mmol, yield of 65%) of Intermediate 28-2 without apurification process. The obtained compound was confirmed by LC-MS.

LC-MS m/z=276 (M+H)⁺

2) Synthesis of Intermediate 28-2

Intermediate 28-2 (yield of 65%) was synthesized in the same manner asCompound 14-2 in Synthesis Example 14, except that Intermediate 28-3 wasused instead of Intermediate 14-3, and Intermediate 17-3 was usedinstead of Intermediate 5-2. The obtained compound was confirmed byLC-MS.

LC-MS m/z=501 (M+H)⁺

3) Synthesis of Intermediate 28-1

Intermediate 28-1 (yield of 98%) was synthesized in the same manner asCompound 21-1 in Synthesis Example 21, except that Intermediate 28-2 wasused instead of Intermediate 21-2. The obtained compound was confirmedby LC-MS.

LC-MS m/z=417 (M+H)⁺

4) Synthesis of Compound 28

0.03 g (1.3 mmol) of NaH was dissolved in 20 ml of anhydrousN,N-dimethylformamide (DMF), and then 0.5 g (1.2 mmol) of Intermediate28-1 was slowly added thereto at a temperature of 0° C. and the resultwas stirred at room temperature for about 1 hour. Next, 0.75 g (1.8mmol) of K₂PtCl₄ dissolved in 10 ml of distilled water was slowly addedthereto, and then the result was stirred at a temperature of 100° C. for6 hours and refluxed while heating for 24 hours. Then, the result wascooled to room temperature, and the obtained solid was filtered andwashed with ether and ethanol. The solid obtained from the above processwas sublimation-purified, thereby obtaining about 0.1 g (0.16 mmol,yield of 13%) of Compound 28.

LC-MS m/z=610 (M+H)⁺

Synthesis Example 29 Synthesis of Compound 29

Compound 29 was synthesized according to Reaction Scheme 29 below:

1) Synthesis of Compound 29

3.0 g (6.0 mmol) of Intermediate 19-1 was dissolved in 40 ml ofdiethylene glycol monoethyl ether, and then 0.9 g (1.0 mmol) ofOs₃(CO)₁₂ was added thereto and the result was stirred at a temperatureof 180° C. for 24 hours. Then, the result was cooled to a temperature of140° C.; 0.4 g (5.0 mmol) of trimethylamine N-oxide was added thereto;and the result was stirred at a temperature of 180° C. for 5 minutes.After 5 minutes, 5.0 mmol of dimethyl(phenyl)phosphine (PPhMe₂) wasadded thereto and the result was stirred for 24 hours. When the reactionwas completed, 80 ml of distilled water was added to the reactionsolution and then, 200 ml of ethyl acetate was added thereto, followedby an extraction process. The extracted organic layer was dried withmagnesium sulfate and distilled under reduced pressure. The result wasseparation-purified by column chromatography and thensublimation-purified, thereby obtaining 3.0 g (3.1 mmol, yield of 52%)of Compound 29.

LC-MS m/z=967 (M+H)⁺

¹H NMR (300 MHz, CDCl₃) δ=9.35 (br s, 2H), 9.02 (br s, 2H), 8.75-8.68(m, 6H), 7.65-7.52 (m, 6H), 7.28-7.22 (m, 4H), 6.51 (s, 2H), 0.81 (m,6H), 0.60 (m, 6H).

Example 1

An anode was prepared by cutting a substrate with ITO/Ag/ITO having athickness of 70/1,000/70 Å deposited thereon to a size of 50 mm×50mm×0.7 mm, ultrasonically cleaning the glass substrate by usingisopropyl alcohol and pure water for 5 minutes each, and thenirradiating UV light for 30 minutes thereto and exposing to ozone toclean. Then, the anode was loaded into a vacuum deposition apparatus.

By vacuum-depositing 2-TNATA on the glass substrate, a hole injectionlayer having a thickness of 600 Å was formed, and then byvacuum-depositing NPB, a hole transport layer having a thickness of1,000 Å was formed.

CBP and Compound 1 were co-deposited on the upper portion of the holetransport layer in a weight ratio of 91:9, thereby forming an emissionlayer having a thickness of 250 Å. BCP was vacuum-deposited on the upperportion of the emission layer, and thus a hole blocking layer having athickness of 50 Å was formed. Alq3 was deposited on the upper portion ofthe hole blocking layer, and thus an electron transport layer having athickness of 350 Å was formed. LiF was vacuum-deposited on the upperportion of the electron transport layer, and thus an electron injectionlayer having a thickness of 10 Å was formed. Then, by vacuum-depositingMg and Ag on the upper portion of the electron injection layer in aweight ratio of 90:10 and forming an electrode having a thickness of 120Å, an organic light-emitting device was manufacture.

Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming an emission layer, Compound 3 wasused instead of Compound 1.

Example 3

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming an emission layer, Compound 5 wasused instead of Compound 1.

Example 4

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming an emission layer, Compound 7 wasused instead of Compound 1.

Example 5

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming an emission layer, Compound 8 wasused instead of Compound 1.

Example 6

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming an emission layer, Compound 9 wasused instead of Compound 1.

Example 7

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming an emission layer, Compound 12 wasused instead of Compound 1.

Example 8

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming an emission layer, Compound 17 wasused instead of Compound 1.

Example 9

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming an emission layer, Compound 27 wasused instead of Compound 1.

Example 10

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming an emission layer, CBP and Compound28 were co-deposited in a weight ratio of 94:6 to form an emission layerhaving a thickness of 400 Å and the thickness of the hole transportlayer was changed to 1,350 Å.

Example 11

An organic light-emitting device was manufactured in the same manner asin Example 10, except that in forming an emission layer, Compound 29 wasused instead of Compound 28.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming an emission layer, Ir(ppy)₃ wasused instead of Compound 1.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming an emission layer, Compound 1-46was used instead of Compound 1.

Comparative Example 3

An organic light-emitting device was manufactured in the same manner asin Example 10, except that in forming an emission layer, PtOEPillustrated below was used instead of Compound 28.

Comparative Example 4

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming an emission layer, Compound Aillustrated below was used instead of Compound 1.

Evaluation Example 1

Driving voltage, current density, brightness, efficiency, emissioncolor, color coordinate and lifespan of Compounds of Examples 1 to 11and Comparative Examples 1 to 4 were measured, and the results are shownin the Table 1 below. LT₉₇ indicates a lifespan, which is a timeduration until brightness reduced to 97% of the initial brightness:

TABLE 1 Driving Current voltage density Brightness Efficiency EmissionColor LT₉₇ Host Dopant (V) (Ma/cm²) (cd/m²) (cd/A) color coordinate (HR)Example 1 CBP Compound 1 5.5 10 5,480 54.8 Green 0.25, 0.70 97 Example 2CBP Compound 3 5.6 10 6,371 63.7 Green 0.24, 0.71 90 Example 3 CBPCompound 5 5.5 10 6,516 65.2 Green 0.25, 0.70 98 Example 4 CBP Compound7 5.6 10 6,296 62.9 Green 0.24, 0.71 95 Example 5 CBP Compound 8 5.7 105,864 58.6 Green 0.23, 0.71 87 Example 6 CBP Compound 9 5.6 10 6,82868.3 Green 0.26, 0.71 94 Example 7 CBP Compound 12 5.8 10 5,735 57.4Green 0.24, 0.70 91 Example 8 CBP Compound 17 5.5 10 6,738 67.4 Green0.23, 0.71 90 Example 9 CBP Compound 27 5.5 10 6,641 66.4 Green 0.28,0.71 93 Example 10 CBP Compound 28 5.6 10 3,570 35.7 Red 0.64, 0.33 95Example 11 CBP Compound 29 5.3 10 3,487 34.8 Red 0.63, 0.34 110Comparative CBP Ir(ppy)₃ 6.8 10 4,766 47.7 Green 0.25, 0.70 61 Example 1Comparative CBP 1-46 6.0 10 5,237 52.3 Green 0.25, 0.73 82 Example 2Comparative CBP PtOEP 7.3 10 2,212 22.1 Red 0.67, 0.32 89 Example 3Comparative CBP Compound A 6.3 10 5,014 50.1 Green 0.29, 0.68 88 Example4

Compounds having a structure represented by Formula 1 according to anembodiment were used in a top-emission type organic light-emittingdevice as a material for a green dopant phosphorescent dopant and a redphosphorescent dopant. As a result, driving voltage was decreased by 0.5volts (V) to 2.0 V; efficiency and lifespan was significantly improvedto have an I-V-L characteristic; brightness was also improved comparedto Ir(ppy)₃, 1-46, PtOEP, and Compound A.

In Example 1, Compound according to embodiment was used as a greenphosphorescent dopant, and thus driving voltage was decreased by 1.3 Vor greater; efficiency was increased by about 15%; and lifespan wasincreased by about 60% compared to Comparative Example 1. Drivingvoltage was decreased by 0.5 V or greater; efficiency was increased byabout 5%; and lifespan was increased by about 20% compared toComparative Example 2.

In Example 11, Compound according to embodiment was used as a redphosphorescent dopant, and thus driving voltage was decreased by 2.0 Vor greater; efficiency was increased by about 55%; and lifespan wasincreased by about 20% compared to Comparative Example 3.

As described above, according to the one or more of the aboveembodiments, the organometallic compound has excellent electriccharacteristics and thermal stability. Accordingly, an organiclight-emitting device including the organometallic compound may have alow driving voltage, high efficiency, high brightness, and a longlifespan.

It should be understood that the exemplary embodiments described thereinshould be considered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments. While one or more embodiments have beendescribed with reference to the figures, it will be understood by thoseof ordinary skill in the art that various changes in form and detailsmay be made therein without departing from the spirit and scope of thepresent disclosure as defined by the following claims.

What is claimed is:
 1. An organometallic compound represented by Formula1:

wherein in Formula 1, M is selected from a Period 1 transition metal, aPeriod 2 transition metal, and a Period 3 transition metal; A₁ ring toA₄ ring are each independently selected from a C₆-C₂₀ carbocyclic groupand a C₁-C₂₀ heterocyclic group, provided that each of A₃ ring and A₄ring is not simultaneously a benzene; X₁ to X₄ are each independentlyselected from C and N; B₁ to B₄ are each independently selected from asingle bond, O, and S; Y₁ and Y₃ are each independently selected from asingle bond and a divalent linking group; Y₂ is selected from asubstituted or unsubstituted C₆-C₆₀ arylene group, a substituted orunsubstituted C₁-C₆₀ heteroarylene group, a substituted or unsubstituteddivalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic hetero-condensed polycyclic group;L₁ is selected from a monodentate ligand and a bidentate ligand; a1 isselected from 0, 1, and 2; R₁ to R₄ are each independently selected froma hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic hetero-condensedpolycyclic group, —C(═O)(Q₁), —Si(Q₁)(Q₂)(Q₃), and —N(Q₁)(Q₂); whereinR₁ and R₄ or R₂ and R₃ are optionally linked to form a saturated orunsaturated ring; Q₁ to Q₃ are each independently selected from a C₁-C₆₀alkyl group and a C₆-C₆₀ aryl group; b1 to b4 are each independentlyselected from 1, 2, 3, and 4; and at least one substituent of thesubstituted C₆-C₆₀ arylene group, substituted C₁-C₆₀ heteroarylenegroup, substituted divalent non-aromatic condensed polycyclic group,substituted divalent non-aromatic hetero-condensed polycyclic group, thesubstituted C₁-C₆₀ alkyl group, substituted C₂-C₆₀ alkenyl group,substituted C₂-C₆₀ alkynyl group, substituted C₁-C₆₀ alkoxy group,substituted C₃-C₁₀ cycloalkyl group, substituted C₁-C₁₀ heterocycloalkylgroup, substituted C₃-C₁₀ cycloalkenyl group, substituted C₁-C₁₀heterocycloalkenyl group, substituted C₆-C₆₀ aryl group, substitutedC₆-C₆₀ aryloxy group, substituted C₆-C₆₀ arylthio group, substitutedC₁-C₆₀ heteroaryl group, substituted monovalent non-aromatic condensedpolycyclic group, and substituted monovalent non-aromatichetero-condensed polycyclic group is selected from a deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group; aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, anda C₁-C₆₀ alkoxy group, each substituted with at least one selected froma deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, and a phosphoric acid group or a salt thereof; and aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic hetero-condensed polycyclic group;
 2. Theorganometallic compound of claim 1, wherein M is a Period 3 transitionmetal.
 3. The organometallic compound of claim 1, wherein A₁ ring to A₄ring are each independently selected from a benzene, a naphthalene, apyrrole, an imidazole, a pyrazole, a thiazole, an isothiazole, anoxazole, an isoxazole, a triazole, indazole, tetrahydroindazole, apyridine, a pyrimidine, a pyrazine, a pyridazine, a triazine, aquinoline, an isoquinoline, a dibenzofuran, and a dibenzothiophene. 4.The organometallic compound of claim 1, wherein A₁ ring to A₄ ring areeach independently selected from a benzene, a pyrazole, an indazole, atetrahydroindazole, a pyridine, a quinoline, an isoquinoline, and adibenzofuran.
 5. The organometallic compound of claim 1, wherein each ofB₁ to B₄ is a single bond.
 6. The organometallic compound of claim 1,wherein Y₁ and Y₃ are each independently selected from a single bond,—O—, —S—, —{B(Q₁₁)}-, —{N(Q₁₂)}-, —{C(Q₁₁)(Q₁₂)}_(n1)-,—{Si(Q₁₁)(Q₁₂)}_(n1)-, a substituted or unsubstituted C₆-C₆₀ arylenegroup, a substituted or unsubstituted C₁-C₆₀ heteroarylene group, asubstituted or unsubstituted divalent non-aromatic condensed polycyclicgroup, and a substituted or unsubstituted divalent non-aromatichetero-condensed polycyclic group; Q₁₁ and Q₁₂ are each independentlyselected from a hydrogen, a deuterium, a C₁-C₆₀ alkyl group, a C₆-C₆₀aryl group, and a C₁-C₆₀ heteroaryl group; and n1 is selected from 1, 2,and
 3. 7. The organometallic compound of claim 1, wherein Y₁ and Y₃ areeach independently selected from a single bond, —O—, —S—, —{B(Q₁₁)}-,—{N(Q₁₁)}-, —{C(Q₁₁)(Q₁₂)}_(n1)-, —{Si(Q₁₁)(Q₁₂)}_(n1)-, a phenylenegroup, a naphthylene group, a fluorenylene group, a pyridinylene group,a pyrazinylene group, a pyrimidinylene group, a quinolinylene group, anisoquinolinylene group, a naphthyridinylene group, a quinoxalinylenegroup, a quinazolinylene group, a dibenzofuranylene group, and adibenzothiophenylene group; and a phenylene group, a naphthylene group,a fluorenylene group, a pyridinylene group, a pyrazinylene group, apyrimidinylene group, a quinolinylene group, an isoquinolinylene group,a naphthyridinylene group, a quinoxalinylene group, a quinazolinylenegroup, a dibenzofuranylene group, and a dibenzothiophenylene group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a methyl group, an ethyl group, an n-propyl group, an iso-propylgroup, an n-butyl group, an iso-butyl group, a sec-butyl group, atert-butyl group, a phenyl group, and a pyridinyl group; Q₁₁ and Q₁₂ areeach independently selected from a hydrogen, a deuterium, a methylgroup, an ethyl group, an n-propyl group, an iso-propyl group, ann-butyl group, an iso-butyl group, a tert-butyl group, and a phenylgroup; and n1 is
 1. 8. The organometallic compound of claim 1, whereinY₁ and Y₃ are each independently selected from a single bond, —O—, —S—,—N(CH₃)—, —N(Ph)-, —CH₂—, —C(CH₃)₂—, —C(CH₃)(Ph)-, —C(Ph)₂- and any oneselected from Formulae 3-1 to 3-17:

wherein in Formulae 3-1 to 3-17, each of * and *′ indicates a bindingsite to a neighboring atom.
 9. The organometallic compound of claim 1,wherein Y₂ is selected from a phenylene group, a naphthylene group, afluorenylene group, a pyridinylene group, a pyrazinylene group, apyrimidinylene group, a quinolinylene group, an isoquinolinylene group,a naphthyridinylene group, a quinoxalinylene group, a quinazolinylenegroup, a dibenzofuranylene group, and a dibenzothiophenylene group; anda phenylene group, a naphthylene group, a fluorenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, aquinolinylene group, an isoquinolinylene group, a naphthyridinylenegroup, a quinoxalinylene group, a quinazolinylene group, adibenzofuranylene group, and a dibenzothiophenylene group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a methyl group, an ethyl group, an n-propyl group, an iso-propylgroup, an n-butyl group, an iso-butyl group, a sec-butyl group, atert-butyl group, a phenyl group, and a pyridinyl group.
 10. Theorganometallic compound of claim 1, wherein Y₂ is selected from aphenylene group, a pyridinylene group, a quinolinylene group, anisoquinolinylene group, a dibenzofuranylene group, and adibenzothiophenylene group; and a phenylene group, a pyridinylene group,a quinolinylene group, an isoquinolinylene group, a dibenzofuranylenegroup, and a dibenzothiophenylene group, each substituted with at leastone selected from a deuterium, a methyl group, a tert-butyl group, and aphenyl group
 11. The organometallic compound of claim 1, wherein Y₂ isselected from Formulae 3-1 to 3-17:

wherein in Formulae 3-1 to 3-17, each of * and *′ indicates a bindingsite to a neighboring atom.
 12. The organometallic compound of claim 1,wherein Y₂ is selected from Formulae 3-1 to 3-11:

wherein in Formulae 3-1 to 3-11, each of * and *′ indicates a bindingsite to a neighboring atom.
 13. The organometallic compound of claim 1,wherein L₁ is a monodentate ligand, and a1 is
 2. 14. The organometalliccompound of claim 1, wherein R₁ to R₄ are each independently selectedfrom a hydrogen, a deuterium, —F, —Cl, —Br, —I, a methyl group, an ethylgroup, an n-propyl group, an iso-propyl group, an n-butyl group, aniso-butyl group, a sec-butyl group, a tert-butyl group, —CF₃, a methoxygroup, an ethoxy group, a tert-butoxy group, a phenyl group, —C(═O)(Q₁),—Si(Q₁)(Q₂)(Q₃), and —N(Q₁)(Q₂); and a phenyl group substituted with amethyl group; wherein R₁ and R₄ or R₂ and R₃ are optionally linked toform a saturated or unsaturated ring; and Q₁ to Q₃ are eachindependently selected from a methyl group, an ethyl group, an n-propylgroup, an iso-propyl group, an n-butyl group, an iso-butyl group, asec-butyl group, a tert-butyl group, and a phenyl group.
 15. Theorganometallic compound of claim 1, wherein R₁ to R₄ are eachindependently selected from a hydrogen, a deuterium, —F, a methyl group,an ethyl group, an n-propyl group, an iso-propyl group, an iso-butylgroup, a sec-butyl group, a tert-butyl group, —CF₃, a methoxy group, atert-butoxy group, a phenyl group, —C(═O)(CH₃), —Si(CH₃)₃, —N(CH₃)₂,—N(Ph)₂, and a group represented by Formula 4-1; wherein R₁ and R₄ or R₂and R₃ are optionally linked to form a saturated or unsaturated ring:

wherein in Formula 4-1, * indicates a binding site to a neighboringatom.
 16. The organometallic compound of claim 1, wherein theorganometallic compound is represented by any one selected from Formulae1-1 to 1-8:

wherein in Formulae 1-1 to 1-8, M, A₁ to A₄, Y₂, L₁, a1, R₁ to R₄, andb1 to b4 are the same as in Formula
 1. 17. The organometallic compoundof claim 1, wherein the organometallic compound is represented by anyone selected from Formulae 1-1 to 1-8:

wherein in Formulae 1-1 to 1-8, M is selected from Os, Ir, and Pt; A₁ring to A₄ ring are each independently selected from a benzene, apyrazole, an indazole, a tetrahydroindazole, a pyridine, a quinoline, anisoquinoline, and a dibenzofuran; and Y₂ is selected from Formulae 3-1to 3-17:

wherein in Formulae 3-1 to 3-17, each of * and *′ indicates a bindingsite to a neighboring atom; R₁ to R₄ are each independently selectedfrom a hydrogen, a methyl group, an ethyl group, an iso-propyl group, aniso-butyl group, a sec-butyl group, a tert-butyl group, —CF₃, a phenylgroup, —Si(CH₃)₃, and a group represented by Formula 4-1;

wherein in Formula 4-1, * indicates a binding site to a neighboringatom; and b1 to b4 are each independently selected from 1, 2, 3, and 4.18. The organometallic compound of claim 1, wherein organometalliccompound is selected from Compounds 1 to 29:


19. An organic light-emitting device comprising: a first electrode; asecond electrode; and an organic layer disposed between the firstelectrode and the second electrode, wherein the organic layer comprisesan emission layer and at least one organometallic compound of claim 1.20. The organic light-emitting device of claim 19, wherein the emissionlayer comprises the organometallic compound of claim 1; the emissionlayer further comprises a host, and the organometallic compound is adopant.